Vacation Rentals In The Berkshires, Vacation Homes Rentals In The Berkshires, Berkshire Summer Home Vacation Rentals, Berkshire Vacation Home Rentals

Vacation Rentals In The Berkshires, Vacation Homes Rentals In The Berkshires, Berkshire Summer Home Vacation Rentals, Berkshire Vacation Home Rentals

 

  

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Vacation Rentals In Lenox MA, Vacation Homes Rentals Lee MA, Stockbridge MA Summer Home Vacation Rentals, Berkshire Vacation Home Rentals

Vacation Rentals In Lenox MA, Vacation Homes Rentals Lee MA, Stockbridge MA Summer Home Vacation Rentals, Berkshire Vacation Home Rentals Vacation Rentals In Lenox MA, Vacation Homes Rentals Lee MA, Stockbridge MA Summer Home Vacation Rentals, Berkshire Vacation Home Rentals Vacation Rentals In Lenox MA, Vacation Homes Rentals Lee MA, Stockbridge MA Summer Home Vacation Rentals, Berkshire Vacation Home Rentals Vacation Rentals In Lenox MA, Vacation Homes Rentals Lee MA, Stockbridge MA Summer Home Vacation Rentals, Berkshire Vacation Home Rentals Vacation Rentals In Lenox MA, Vacation Homes Rentals Lee MA, Stockbridge MA Summer Home Vacation Rentals, Berkshire Vacation Home Rentals Vacation Rentals In Lenox MA, Vacation Homes Rentals Lee MA, Stockbridge MA Summer Home Vacation Rentals, Berkshire Vacation Home Rentals Vacation Rentals In Lenox MA, Vacation Homes Rentals Lee MA, Stockbridge MA Summer Home Vacation Rentals, Berkshire Vacation Home Rentals
 

Berkshire Vacation Rentals

 

Vacation rentals in the Berkshires make for a memorable Berkshire vacation. Stay at one of the many vacation home rentals throughout the Berkshires. From vacation homes for rent to vacation apartment and condo rentals, each vacation rental offers a truly unique lodging experience. Below, you will find vacation home rentals in the Northern Berkshires, Central Berkshires and Southern Berkshires. Many vacation rentals are located within a short distance to one of our wonderful Berkshire attractions such as Tanglewood, MASS MoCA, The Colonial Theatre, Norman Rockwell Museum, Barrington Stage Company, Williamstown Theatre Festival, Clark Art, Ski Areas, Colleges and more!

 
Vacation Rentals In Adams MA, Vacation Rentals In The Berkshires, Vacation Home Rentals In The Berkshires, Vacation Homes For Rent In The Berkshires
A Beautiful Place To Enjoy The
Beautiful Berkshires!.
Adams, MA
Sleeps: 14
Bedrooms: 7
Bathrooms: 3.5
No Pets
Vacation Rental Rates & Availability
 
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Peaceful Berkshires Retreat. Enjoy All Seasons In The Amazing Berkshires.
Alford, MA
Sleeps: 10
Bedrooms: 3
Bathrooms: 3
No Pets
Vacation Rental Rates & Availability
 
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Luxury Suite @ Smith Homestead.
Over 25 Acres Of Fields And Woods.
Alford, MA
Sleeps: 2
Bedrooms: 1
Bathrooms: 1
No Pets
Vacation Rental Rates & Availability
 
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Beautiful Berkshire Farm House On
More Then 1,000 Feet Of Green River.
Alford, MA
Sleeps: 16
Bedrooms: 6
Bathrooms: 4.5
Pets Considered
Vacation Rental Rates & Availability
 
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Case Mill-Secluded Berkshire, Pond,
Farmhouse, Mill, Waterfall, 28 Acres.
Alford, MA
Sleeps: 7
Bedrooms: 3
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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1700's Colonial In The Berkshires,
Great Barrington, Town Of Alford.
Alford, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 1
Pets Considered
Vacation Rental Rates & Availability
 
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5,000 Sq. Ft Of Luxury And Every
Amenity In A Stunning Rustic Setting.
Becket, MA
Sleeps: 10
Bedrooms: 4
Bathrooms: 3.5
Pets Considered
Vacation Rental Rates & Availability
 
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Starry Nite - Lake & Mountain Getaway.
Summer 2018 Dates Open!!!
Becket, MA
Sleeps: 10
Bedrooms: 3
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Beautiful Lakefront Home On Tree
Lined Property In The Berkshires.
Becket, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 2.5
No Pets
Vacation Rental Rates & Availability
 
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Beautiful Direct Lakefront Cottage
In The Berkshires.
Becket, MA (Sherwood Forest)
Sleeps: 6
Bedrooms: 2
Bathrooms: 1
No Pets
Vacation Rental Rates & Availability
 
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Quiet Comfortable Cabin 5 Minute
Walk To Swimming And Boating.
Becket, MA (Sherwood Forest)
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
Pets Considered
Vacation Rental Rates & Availability
 
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Direct Waterfront Cottage On Pristine
Lake In The Berkshires.
Becket, MA
Sleeps: 6
Bedrooms: 2
Bathrooms: 1
No Pets
Vacation Rental Rates & Availability
 
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Berkshires Cottage Nestled In Woods,
Within 1 Minute Of Tranquil Lake.
Becket, MA
Sleeps: 6
Bedrooms: 2
Bathrooms: 1
Pets Considered
Vacation Rental Rates & Availability
 
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A-Frame In Sherwood Forest.
Easy Walk To Peaceful Lake,
Becket, MA (Sherwood Forest)
Sleeps: 5
Bedrooms: 1
Bathrooms: 1
Pets Considered
Vacation Rental Rates & Availability
 
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Affordable Country Living Post &
Beam Schoolhouse, Babbling Brook.
Becket, MA
Sleeps: 6
Bedrooms: 5
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Charming Post & Beam, Year-Round, Family-Friendly Berkshire Home.
Becket, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Serene, Private Waterfront House --Perfect Summer Retreat!
Becket, MA (Sherwood Forest)
Sleeps: 6
Bedrooms: 2
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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3 Miles To Jacob's Pillow, Clearing In
The Forest, Clean And New!
Becket, MA (Sherwood Forest)
Sleeps: 11
Bedrooms: 3
Bathrooms: 2.5
Pets Considered
Vacation Rental Rates & Availability
 
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Peace And Quiet On The Lake
In Sherwood Forest.
Becket, MA (Sherwood Forest)
Sleeps: 6
Bedrooms: 2
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Comfortable Berkshire Home,
2 Bed/Bath; AC; Fireplace; Keyboard.
Becket, MA
Sleeps: 6
Bedrooms: 2
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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Bright, Cozy Berkshire Cottage
Across From Pristine Lake.
Becket, MA (Sherwood Forest)
Sleeps: 8
Bedrooms: 2
Bathrooms: 1
Pets Considered
Vacation Rental Rates & Availability
 
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Beautifully Renovated Old Colonial
In Secluded Berkshires.
Becket, MA
Sleeps: 11
Bedrooms: 7
Bathrooms: 2.5
Pets Considered
Vacation Rental Rates & Availability
 
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Charming Berkshire Cottage
5 Minutes From Jacob's Pillow.
Becket, MA
Sleeps: 4
Bedrooms: 3
Bathrooms: 1
No Pets
Vacation Rental Rates & Availability
 
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Beautifully Appointed Contemporary
3,200 Sq. Ft. Retreat on Yokum Pond.
Becket, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 4
No Pets
Vacation Rental Rates & Availability
 
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Beautiful 4 Season Lakeside Log
Home Close To Berkshires Attractions.
Becket, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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Beautiful Spacious Wooded Home.
Sunny With Open Living Area.
Becket, MA
Sleeps: 12
Bedrooms: 4
Bathrooms: 2.5
No Pets
Vacation Rental Rates & Availability
 
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Sprawling Ranch Nestled In Private Wooded Lot With Expansive Yards!.
Becket, MA
Sleeps: 8
Bedrooms: 4
Bathrooms: 3.5
Pets Considered
Vacation Rental Rates & Availability
 
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Large, 19th Century Fully Renovated Historic Barn In The Berkshires.
Cheshire, MA
Sleeps: 10
Bedrooms: 3
Bathrooms: 1
Pets Considered
Vacation Rental Rates & Availability
 
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Brooksong, The Perfect Berkshire Mountain Getaway On 5+ Acres.
Dalton, MA
Sleeps: 10
Bedrooms: 5
Bathrooms: 2.5
No Pets
Vacation Rental Rates & Availability
 
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Inviting Berkshire Home In
Village Of Egremont.
Egremont, (South Egremont) MA
Sleeps: 10
Bedrooms: 3
Bathrooms: 1.5
No Pets
Vacation Rental Rates & Availability
 
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Charming Lakefront Home In The
Heart Of The Berkshires.
Egremont, MA
Sleeps: 7
Bedrooms: 3
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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Antique Farmhouse, Gourmet Kitchen, Farmstay, 2 Acres, Chickens, Sheep.
Egremont, (North Egremont) MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Studio Apt. In Quiet Country Setting, 3
Miles From Downtown Gr. Barrington.
Egremont, MA
Sleeps: 3
Bedrooms: Studio
Bathrooms: 1
No Pets
Vacation Rental Rates & Availability
 
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Renovated Ski House Sleeps 11, Catamount 3 Miles.
Egremont, MA
Sleeps: 11
Bedrooms: 4
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Beautiful Berkshire Retreat, Well Maintained Home, Stunning Views.
Egremont, MA
Sleeps: 12
Bedrooms: 5
Bathrooms: 4.5
No Pets
Vacation Rental Rates & Availability
 
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Across From Catamount,
Newley Renovated Contemporary!
Egremont, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 3
No Pets
Vacation Rental Rates & Availability
 
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Idyllic Berkshire Get Away: Balance
Of Relaxation And Convenience.
Great Barrington, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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Great Barrington Family And Dog
Friendly Retreat From The City!
Great Barrington, MA
Sleeps: 8
Bedrooms: 4
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Ideal Location, Freshly Renovated,
Quiet 3BR/2BA In-Town Home.
Great Barrington, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Chic Berkshire Carriage House.
Pets Considered.
Great Barrington, MA
Sleeps: 5
Bedrooms: 2
Bathrooms: 1
Pets Considered
Vacation Rental Rates & Availability
 
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Cozy Log Home With Open Floor Plan, Deck, Nice Yard, Fireplace & More.
Great Barrington, MA
Sleeps: 10
Bedrooms: 2
Bathrooms: 1
Pets Considered
Vacation Rental Rates & Availability
 
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Minutes From Downtown Great
Barrington, Convenient Location.
Great Barrington, MA
Sleeps: 8
Bedrooms: 4
Bathrooms: 3
No Pets
Vacation Rental Rates & Availability
 
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Berkshires, MA, Close to Tanglewood,
Jacob's PIllow, Berkshire Theater.
Great Barrington, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Family Home, Big Yard, Short Walk
To Downtown And Lake Mansfield.
Great Barrington, MA
Sleeps: 8
Bedrooms: 4
Bathrooms: 1.5
Pets Considered
Vacation Rental Rates & Availability
 
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Peaceful Two Bedroom Schoolhouse
Cottage In The Berkshires.
Great Barrington, MA
Sleeps: 5
Bedrooms: 2
Bathrooms: 1
Pets Considered
Vacation Rental Rates & Availability
 
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Classic Charm And Comfort In This
Private, Renovated Home.
Great Barrington, MA
Sleeps: 8
Bedrooms: 4
Bathrooms: 2.5
No Pets
Vacation Rental Rates & Availability
 
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Family Vacation Home In Great
Barrington On 3 Secluded Acres.
Great Barrington, MA
Sleeps: 9
Bedrooms: 4
Bathrooms: 3
Pets Considered
Vacation Rental Rates & Availability
 
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1840's Restored Barn! Exposed
Beams! Private! 3 Minutes To Lake.
Great Barrington, MA
Sleeps: 10
Bedrooms: 5
Bathrooms: 2.5
Pets Considered
Vacation Rental Rates & Availability
 
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Perfect Location Retreat! Minutes to
Downtown & Butternut!.
Great Barrington, MA
Sleeps: 7
Bedrooms: 3
Bathrooms: 1.5
No Pets
Vacation Rental Rates & Availability
 
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Knob Hill Great Barrington, MA. Walk
To Lake Mansfield & Center Of Town.
Great Barrington, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 1
Pets Considered
Vacation Rental Rates & Availability
 
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Wonderful Spot in The Heart of The
Berkshires On 9 Private Acres.
Great Barrington, MA
Sleeps: 8
Bedrooms: 4
Bathrooms: 2.5
No Pets
Vacation Rental Rates & Availability
 
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5 Bedroom Great Barrington House
With Mountain Views On 30 Acres!
Great Barrington, MA
Sleeps: 10
Bedrooms: 5
Bathrooms: 4
No Pets
Vacation Rental Rates & Availability
 
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NEW! Charming 3 Bedroom Great
Barrington House By River!
Great Barrington, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Great Barrington On "The Hill"
Private Location Yet Close To It All.
Great Barrington, MA
Sleeps: 10
Bedrooms: 4
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Spacious Comfortable Year-Round Vacation Home For 10+.
Great Barrington, MA
Sleeps: 10
Bedrooms: 5
Bathrooms: 3
No Pets
Vacation Rental Rates & Availability
 
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Lovely, Large & Comfortable, Located
"On The Hill" In Great Barrington.
Great Barrington, MA
Sleeps: 8
Bedrooms: 4
Bathrooms: 4.5
Pets Considered
Vacation Rental Rates & Availability
 
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Pristine Victorian: Short Walk
To Lake Or Town!
Great Barrington, MA
Sleeps: 10
Bedrooms: 5
Bathrooms: 3.5
No Pets
Vacation Rental Rates & Availability
 
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Bigger Views With Heated Pool, Hot
Tub, Workout Room, Sauna And More.
Great Barrington, MA
Sleeps: 14
Bedrooms: 6
Bathrooms: 4
Pets Considered
Vacation Rental Rates & Availability
 
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Maya's Garden House, Located Less
Than 1 Mile From Butternut Basin.
Great Barrington, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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In Town 5-Bedroom Colonial In
A Park-Like Setting.
Great Barrington, MA
Sleeps: 8
Bedrooms: 5
Bathrooms: 4
No Pets
Vacation Rental Rates & Availability
 
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Open Field House With A View!
Dog Friendly.
Great Barrington, MA
Sleeps: 5
Bedrooms: 3
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Charming Log Home,
Well-Located In Great Barrington.
Great Barrington, MA
Sleeps: 10
Bedrooms: 4
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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Location Location! Comfort And
Privacy So Close To Downtown.
Great Barrington, MA
Sleeps: 10
Bedrooms: 5
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
Click Here To View All Great Barrington, MA Vacation Rentals
 
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Contemporary 'Castle In The Sky'
On 15 Acres.
Lanesborough, MA
Sleeps: 6
Bedrooms: 2
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Completely Remodeled Country Waterfront Lakehouse - Berkshires.
Lanesboro, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 1.5
Pets Considered
Vacation Rental Rates & Availability
 
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Charming Historic Cottage On Scenic
Road To Mt. Greylock.
Lanesboro, MA
Sleeps: 6
Bedrooms: 2
Bathrooms: 1
No Pets
Vacation Rental Rates & Availability
 
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Spacious Traditional Country
Farmhouse On 27 Secluded Acres.
Lanesboro, MA
Sleeps: 12
Bedrooms: 4
Bathrooms: 2.5
Pets Considered
Vacation Rental Rates & Availability
 
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New Huge Beautiful House - 16 Acres
2 Miles From Jiminy!.
Lanesboro, MA
Sleeps: 10
Bedrooms: 3
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Private Home, Large Yard, Minutes
From Jimny Peak/Tanglewood.
Lanesboro, MA
Sleeps: 17
Bedrooms: 6
Bathrooms: 3.5
No Pets
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Create Lasting Family Memories
In Massachusetts.
Lanesboro, MA
Sleeps: 8
Bedrooms: 2
Bathrooms: 2
No Pets
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Jiminy Peak 4 Level Luxury All Year
Round Condo Also Winter Ski Rental.
Lanesboro, MA
Sleeps: 10
Bedrooms: 4
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Beautifully Decorated Mountainside
Unit, Steps From Chairlift.
Lanesboro, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
No Pets
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The Playhouse: 7,000 Square Feet Of
Berkshires Modern Luxury And History.
Lee, MA
 Sleeps: 20
Bedrooms: 6
Bathrooms: 5
Pets Considered
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Lovingly Restored Victorian In
Lee's Historic District.
Lee, MA
Sleeps: 12
Bedrooms: 5
Bathrooms: 5
Pets Considered
Vacation Rental Rates & Availability
 
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Enjoy Relaxing Organic Living In The
Heart of the Berkshires!
Lee, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
Pets Considered
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Tanglewood/Downtown Lenox, Lee,
Stockbridge 5 Minutes Or Less.
Lee, MA
Sleeps: 15
Bedrooms: 5
Bathrooms: 3.5
No Pets
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Spacious Comfortable Charming
Family Farmhouse Great Location.
Lee, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
No Pets
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Modern And Spacious Berkshires Retreat - 5 Bedrooms & 3 Baths.
Lee, MA
Sleeps: 10
Bedrooms: 5
Bathrooms: 3
No Pets
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Spectacular Setting On Your Own
Private Lake Close To It All.
Lee (South Lee), MA
Sleeps: 10
Bedrooms: 4
Bathrooms: 3
Pets Considered
Vacation Rental Rates & Availability
 
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A Luxurious Retreat In The Secluded
Hills Of Old New England.
Lee (South Lee), MA
Sleeps: 8
Bedrooms: 4
Bathrooms: 3.5
No Pets
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Holiday Inn Club/Oak And Spruce
Resort, Berkshires.
Lee (South Lee), MA
Sleeps: 6
Bedrooms: 2
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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A Small Oasis In The Heart Of Lenox.
A Tanglewood-Lover's Haven!
Lenox, MA
Sleeps: 3
Bedrooms: 1
Bathrooms: 1
Pets Considered
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1898 Refurbished Farmhouse - Easy
Walk To Lenox Center.
Lenox, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 2.5
Pets Considered
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Secluded Luxury, Situated Between
Tanglewood And Historic Lenox.
Lenox, MA
Sleeps: 15
Bedrooms: 5
Bathrooms: 3.5
No Pets
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Large Cape Across From
Cranwell Golf & Spa Resort.
Lenox, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
No Pets
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Unique Lenox Condo, Quiet Neighborhood, Walk to Town..
Lenox, MA
Sleeps: 4
Bedrooms: 2
Bathrooms: 2
No Pets
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Charming, Spacious Home, Stunning
Views, Steps From Tanglewood!
Lenox, MA
Sleeps: 14
Bedrooms: 5
Bathrooms: 5.5
No Pets
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Charming Lenox Cottage Within
Walking Distance To Town.
Lenox, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
Pets Considered
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The best of both worlds, Country and
Culture In The Berkshires.
Lenox, MA
Sleeps: 8
Bedrooms: 5
Bathrooms: 3
No Pets
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Lenox Haus Close To Downtown,
Quiet Neighborhood, Dead End Street.
Lenox, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
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Lovely Home In Heart Of Lenox & Just
Minutes From Tanglewood By Car.
Lenox, MA
Sleeps: 4
Bedrooms: 2
Bathrooms: 2
No Pets
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22 Acre Historical Compound
Walking Distance To Lenox Center.
Lenox, MA
Sleeps: 15
Bedrooms: 8
Bathrooms: 4.5
Pets Considered
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Brand New Unit At The Walker House Residences In Downtown Lenox.
Lenox, MA
Sleeps: 4
Bedrooms: 2
Bathrooms: 1.5
No Pets
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Lemon Cottage Walk to Town/Tanglewood.
Lenox, MA
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
No Pets
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Large Immaculate Home, 10 Minute
Walk To Lenox Center.
Lenox, MA
Sleeps: 8
Bedrooms: 4
Bathrooms: 3.5
Pets Considered
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Hidden Gem In Lenox Great Estate.
Minutes To Idyllic Lenox Center.
Lenox, MA
Sleeps: 4
Bedrooms: 2
Bathrooms: 1.5
No Pets
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Clean Mid-Century Modern Home Near
Tanglewood With Gourmet Kitchen.
Lenox, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
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3 Minutes To Lenox Center And
Set On 5 Wooded Acres.
Lenox, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 1
Pets Considered
Vacation Rental Rates & Availability
 
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Newly Renovated 3 BR Haus In Lenox With Modern Interior Design.
Lenox, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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Come Vacation In Beautiful Lenox In
The Heart Of The Berkshires!
Lenox, MA
Sleeps: 10
Bedrooms: 3
Bathrooms: 2.5
No Pets
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Lenox Waterfront Cottage - Tranquil
Escape, near Berkshire Attractions.
Lenox, MA
Sleeps: 4
Bedrooms: 2
Bathrooms: 1.5
No Pets
Vacation Rental Rates & Availability
 
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5 STAR! Lenox Vacation Home.
Private, Luxury, Perfect Location.
Lenox, MA
Sleeps: 8
Bedrooms: 4
Bathrooms: 3.5
Pets Considered
Vacation Rental Rates & Availability
 
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Peaceful, Newly Renovated Lakeside Cottage On Lake Garfield - Berkshires.
Monterey, MA
Sleeps: 5
Bedrooms: 2
Bathrooms: 1
Pets Considered
Vacation Rental Rates & Availability
 
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Year Round Relaxation And Activities
For The Whole Family!
Monterey, MA
Sleeps: 8
Bedrooms: 4
Bathrooms: 4.5
Pets Considered
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Cozy Family Chalet, Minutes From
Lake & 10 Minutes From Butternut!.
Monterey, MA
Sleeps: 6
Bedrooms: 2
Bathrooms: 1
Pets Considered
Vacation Rental Rates & Availability
 
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Family-Friendly In The Heart Of
Southern Berkshire County.
Monterey, MA
Sleeps: 8
Bedrooms: 4
Bathrooms: 1.5
Pets Considered
Vacation Rental Rates & Availability
 
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Secluded Hilltop Getaway,
Post & Beam Monterey Home (WIFI).
Monterey, MA
Sleeps: 8
Bedrooms: 4
Bathrooms: 3
No Pets
Vacation Rental Rates & Availability
 
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Beautiful Waterfront House Rental,
Right On Lake Garfield.
Monterey, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Charming Family Lake House.
Waterfront Home On Lake Garfield.
Monterey, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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Berkshire Lake House On Lake
Garfield, Monterey MA - 4 Bedrooms
Monterey, MA
Sleeps: 10
Bedrooms: 4
Bathrooms: 3
Pets Considered
Vacation Rental Rates & Availability
 
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Waterfront Lake House Near Great
Skiing Butternut Basin & Catamount.
Monterey, MA
Sleeps: 9
Bedrooms: 4
Bathrooms: 1.5
No Pets
Vacation Rental Rates & Availability
 
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Light, Airy And Fabulous.
3 Minutes To Lake Garfield!
Monterey, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 2.5
Pets Considered
Vacation Rental Rates & Availability
 
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Renovated Charm - Dock On Lake Garfield, WiFi, Kayaks, Canoe, Etc.
Monterey, MA
Sleeps: 8
Bedrooms: 5
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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Gorgeous Log Cabin On 10 Wooded
Acres In The Berkshires.
Monterey, MA
Sleeps: 9
Bedrooms: 3
Bathrooms: 3
No Pets
Vacation Rental Rates & Availability
 
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Beautiful Lakeside Home In The North
Adams/Williamstown Area.
North Adams, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 1.5
No Pets
Vacation Rental Rates & Availability
 
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Lake House In The Berkshires.
Charming Cottage on Windsor Lake.
North Adams, MA
Sleeps: 2
Bedrooms: 1
Bathrooms: 1
No Pets
Vacation Rental Rates & Availability
 
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Private Post And Beam House With
The Best Views In The Berkshires.
North Adams, MA
Sleeps: 4
Bedrooms: 2
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Large Duplex Near MASS MoCA
MCLA, Recent Complete Renovation.
North Adams, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 1
No Pets
Vacation Rental Rates & Availability
 
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Sweet Berkshire Getaway,
Located Across From Windsor Lake.
North Adams, MA
Sleeps: 3
Bedrooms: 2
Bathrooms: 1.5
No Pets
Vacation Rental Rates & Availability
 
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Spacious 3 Bedroom Victorian
Duplex Near MASS MoCA, MCLA.
North Adams, MA
Sleeps: 5
Bedrooms: 3
Bathrooms: 1.5
No Pets
Vacation Rental Rates & Availability
 
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Luxury Home In Scenic Wooded Area
With Private Lake, Sleeps 16.
Otis, MA
Sleeps: 16
Bedrooms: 4
Bathrooms: 2.5
Pets Considered
Vacation Rental Rates & Availability
 
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4BR Lakefront/Ski House, Internet,
Game Room w/Pool, Ping Pong.
Otis, MA
Sleeps: 10
Bedrooms: 4
Bathrooms: 3
No Pets
Vacation Rental Rates & Availability
 
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Serene, Quiet, Comfortable 3 BR,
2.5 BA Berkshire Vacation Home.
Otis, MA
Sleeps: 7
Bedrooms: 3
Bathrooms: 2.5
No Pets
Vacation Rental Rates & Availability
 
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Quaint 3 BR Lakefront Cottage On
Big Pond In The Berkshires.
Otis, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 1
No Pets
Vacation Rental Rates & Availability
 
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Cozy Waterfront House On Otis
Reservoir With Great Views.
Otis, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 1
No Pets
Vacation Rental Rates & Availability
 
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Private And Cozy At The
Rocke N Horse Farm.
Otis, MA
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
Pets Considered
Vacation Rental Rates & Availability
 
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Waterfront On Big Pond And Benton
Pond Plus 43 Acres Of Private Trails.
Otis, MA
Sleeps: 5
Bedrooms: 3
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Get away From It All. Chalet Home In
Desirable Otis Wood Lands.
Otis, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 2.5
No Pets
Vacation Rental Rates & Availability
 
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Private & Very Secluded 10 Acres
With River "Hansel & Gretel".
Otis, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Sunset Place - Otis Reservoir - Spectacular Lakefront House!
Otis, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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Lake House By Otis Reservoir,
Jacob's Pillow And Tanglewood.
Otis, MA
Sleeps: 7
Bedrooms: 3
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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Modern Secluded 2,500 Sq. Ft. Home
In Wooded Setting.
Otis, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 2.5
No Pets
Vacation Rental Rates & Availability
 
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Swiss Chalet Style Timber Frame
Home With All Modern Conveniences.
Peru, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Peaceful Waters/Private Lake View Sweet Suite.
Pittsfield, MA
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets
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Spacious Contemporary DOWNHILL Condo At The Pines at Bousquet.
Pittsfield, MA
Sleeps: 13
Bedrooms: 3
Bathrooms: 3
Pets Considered
Vacation Rental Rates & Availability
 
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Berkshires Pontoosuc Lake Beauty - Beautifully Renovated Lakefront home.
Pittsfield, MA
Sleeps: 12
Bedrooms: 4
Bathrooms: 3.5
No Pets
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Newly Renovated 4 Bedroom
Lakefront House In The Berkshires.
Pittsfield, MA
Sleeps: 10
Bedrooms: 4
Bathrooms: 2.5
No Pets
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Beautiful Waterfront Home With
Deep Water Dock On Onota Lake.
Pittsfield, MA
Sleeps: 12
Bedrooms: 3
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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Luxury Berkshires Getaway
Ski On Ski Off.
Pittsfield, MA
Sleeps: 10
Bedrooms: 4
Bathrooms: 2.5
No Pets
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Peace & Tranquility Is Our Property's Trademark - Come Get Some!.
Pittsfield, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 1
Pets Considered
Vacation Rental Rates & Availability
 
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Beautiful 7 Bedroom W/Hot Tub &
Pool Table, Walk To Lake.
Pittsfield, MA
Sleeps: 18
Bedrooms: 7
Bathrooms: 3
Pets Considered
Vacation Rental Rates & Availability
 
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Historic Red Schoolhouse Featured
In 2015 Home & Garden TV Special.
Pittsfield, MA
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
Pets Considered
Vacation Rental Rates & Availability
 
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Interior Designers
Botanical Garden Hideaway.
Pittsfield, MA
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets
Vacation Rental Rates & Availability
 
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Spacious Berkshire Summer Rental, Private Dock On Lake 3 BR/2BA.
Pittsfield, MA
Sleeps: 7
Bedrooms: 3
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Lake View w/Kayaks, Fire Pit, Bikes, Swing Set, Near Berkshires Attractions.
Richmond, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 1
Pets Considered
Vacation Rental Rates & Availability
 
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Beautiful House By Richmond Pond Minutes To All Berkshire Attractions.
Richmond, MA
Sleeps: 6
Bedrooms: 2
Bathrooms: 1
No Pets
Vacation Rental Rates & Availability
 
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Charm Upon Charm Every Season
Near Tanglewood Central Location.
Richmond, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 4
Pets Considered
Vacation Rental Rates & Availability
 
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Spacious 4 BR, Bright Contemporary
Home, Tennis, Lake, Gym, Pool.
Sandisfield, MA
Sleeps: 8
Bedrooms: 4
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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Sandisfield, Berkshires, Secluded
Lake Cottage On Private Estate.
Sandisfield, MA
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
No Pets
Vacation Rental Rates & Availability
 
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Berkshires Finest Country Estate In Stunning Setting, 130 Private Acres.
Sandisfield, MA
Sleeps: 18
Bedrooms: 6
Bathrooms: 4
No Pets
Vacation Rental Rates & Availability
 
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Relax, Read, Entertain, Or Walk To
West Lake From Our Berkshire Home.
Sandisfield, MA
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
No Pets
Vacation Rental Rates & Availability
 
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Newly Renovated Country Retreat
With Mountain Views.
Sheffield, MA
Sleeps: 7
Bedrooms: 3
Bathrooms: 3
No Pets
Vacation Rental Rates & Availability
 
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Serene Berkshire Artist's House
Situated On 5 Quiet Acres.
Sheffield, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 2.5
No Pets
Vacation Rental Rates & Availability
 
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Elterwater--Sought After And Rare
Private Idyllic Berkshire Lakefront.
Sheffield, MA
Sleeps: 4
Bedrooms: 3
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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A Comfortable Berkshire Getaway.
Great For Families Or Couples.
Sheffield, MA
Sleeps: 6
Bedrooms: 6
Bathrooms: 2.5
No Pets
Vacation Rental Rates & Availability
 
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Beautiful House, Featured In
"Country Living" Magazine.
Sheffield, (Ashley Falls) MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Private Log Cabin Vacation Rental,
Perfect Summer Getaway, Central AC.
Sheffield, MA
Sleeps: 10
Bedrooms: 4
Bathrooms: 3
Pets Considered
Click Here For Rates & Availability
 
4 Bedroom On Country Road,
5 Miles To Tanglewood.
Stockbridge, MA
Sleeps: 6
Bedrooms: 4
Bathrooms: 3
Pets Considered
Click Here For Rates & Availability
 
One Of The Finest Homes and Best
Location In The Berkshires.
Stockbridge, MA
Sleeps: 11
Bedrooms: 4
Bathrooms: 3
Pets Considered
Click Here For Rates & Availability
 

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Cultural Playground Of The East 2+
Bed Cottage, Walk To Red Lion Inn.
Stockbridge, MA
Sleeps: 7
Bedrooms: 2
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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5,500 Sq. Ft. General Williams
Estate House Lenox/Stockbridge.
Stockbridge, MA
Sleeps: 16
Bedrooms: 6
Bathrooms: 5.5
No Pets
Vacation Rental Rates & Availability
 
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Location!!! Berkshire Glamour (and
comfort) Meets Town And Country.
Stockbridge, MA
Sleeps: 10
Bedrooms: 3
Bathrooms: 3
Pets Considered
Vacation Rental Rates & Availability

 
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Beautiful Berkshire Cabin Close To
All Attractions And Beach.
Stockbridge, MA
Sleeps: 8
Bedrooms: 2
Bathrooms: 1
Pets Considered
Vacation Rental Rates & Availability
 
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Stockbridge! 1/2 Mile From Red Lion
Inn. Gt. Barrington, Lenox, Lee Close.
Stockbridge, MA
Sleeps: 12
Bedrooms: 4
Bathrooms: 3.5
No Pets
Vacation Rental Rates & Availability
 
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Modern, Secluded Cottage In The
Heart Of The Berkshires!.
Stockbridge, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 2.5
Pets Considered
Vacation Rental Rates & Availability
 
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NEW! 2 Bedroom Stockbridge Home
Walk To Golf Course!
Stockbridge, MA
Sleeps: 6
Bedrooms: 2
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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Family Getaway In Stockbridge Woods Mins. To Tanglewood, Lenox & GB.
Stockbridge, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Cozy Modern Rental (Minutes From
Lenox, Kripalu & Tanglewood).
Stockbridge, MA
Sleeps: 6
Bedrooms: 2
Bathrooms: 1
Pets Considered
Vacation Rental Rates & Availability
 
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Escape To Stockbridge, 1 Mile To
Red Lion Inn, Complete Privacy!
Stockbridge, MA
Sleeps: 8
Bedrooms: 4
Bathrooms: 3
No Pets
Vacation Rental Rates & Availability
 
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Tranquil 3 Bedroom Stockbridge
House With Private Deck.
Stockbridge, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 1.5
No Pets
Vacation Rental Rates & Availability
 
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Gorgeous Stockbridge Bowl
Beach/Tanglewood.
Stockbridge, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 1.5
No Pets
Vacation Rental Rates & Availability
 
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Spectacular Housatonic River View,
Newly Renovated Historic Cottage.
Stockbridge, MA
Sleeps: 4
Bedrooms: 2
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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Rustic Waterfront Retreat With Private Dock & Canoe On Stockbridge Bowl..
Stockbridge, MA
Sleeps: 6
Bedrooms: 2
Bathrooms: 1
No Pets
Vacation Rental Rates & Availability
 
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Family-Friendly Cottage Off Lake in Stockbridge.
Stockbridge, MA
Sleeps: 7
Bedrooms: 4
Bathrooms: 1.5
No Pets
Vacation Rental Rates & Availability
 
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Charming Newly Renovated Lakefront
Cottage On Stockbridge Bowl.
Stockbridge, MA
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
No Pets
Vacation Rental Rates & Availability
 
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Convenient to Beach, Tanglewood
And All Berkshire Amenities.
Stockbridge, MA
Sleeps: 6
Bedrooms: 2
Bathrooms: 1
Pets Considered
Vacation Rental Rates & Availability
 
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Charming Historic Home A Stones
Throw Away From The Red Lion Inn.
Stockbridge, MA
Sleeps: 22
Bedrooms: 11
Bathrooms: 7.5
Pets Considered
Vacation Rental Rates & Availability
 
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Centrally Located Contemporary
Gem In Stockbridge.
Stockbridge, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 2.5
Pets Considered
Vacation Rental Rates & Availability
 
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Stockbridge Bowl: Quaint Waterfront
Cottage For Your Summer Home!!.
Stockbridge, MA
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
No Pets
Vacation Rental Rates & Availability
 
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Charming Home In A Bucolic Setting,
Near Berkshire Botanical Gardens.
Stockbridge, MA
Sleeps: 5
Bedrooms: 3
Bathrooms: 1
No Pets
Vacation Rental Rates & Availability
 
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Stockbridge Classic 1880 Farmhouse
Newly Renovated.
Stockbridge, MA
Sleeps: 8
Bedrooms: 4
Bathrooms: 3.5
No Pets
Vacation Rental Rates & Availability
 
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Modern Home With Stockbridge Bowl Access, 5 Minutes To Tanglewood.
Stockbridge, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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A Charming Mid 1800's
Stockbridge Farmhouse.
Stockbridge, MA
Sleeps: 7
Bedrooms: 4
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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NEW! 'Butterfly Hill' 2 Bedroom
West Stockbridge House.
West Stockbridge, MA
Sleeps: 4
Bedrooms: 2
Bathrooms: 1.5
No Pets
Vacation Rental Rates & Availability
 
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Family Friendly Colonial In
Berkshire County On 6 Acres.
West Stockbridge, MA
Sleeps: 10
Bedrooms: 5
Bathrooms: 3
Pets Considered
Vacation Rental Rates & Availability
 
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Quiet Retreat Close To
All Things Berkshire.
West Stockbridge, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 2.5
Pets Considered
Vacation Rental Rates & Availability
 
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On the Williams River in
Downtown West Stockbridge.
West Stockbridge, MA
Sleeps: 5
Bedrooms: 2
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Perfect Setting For Family Vacations Reunions & Special Occasion Events.
West Stockbridge, MA
Sleeps: 10
Bedrooms: 5
Bathrooms: 5
No Pets
Vacation Rental Rates & Availability
 
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Rare Setting Overlooking River,
West Stockbridge Dream.
West Stockbridge, MA
Sleeps: 8
Bedrooms: 2
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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Beautiful Family Farmhouse In
Williamstown, MA.
Williamstown, MA
Sleeps: 10
Bedrooms: 6
Bathrooms: 3
Pets Considered
Vacation Rental Rates & Availability
 
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Cozy And Quaint Country Cottage,
Walk To Downtown Williamstown.
Williamstown, MA
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
Pets Considered
Vacation Rental Rates & Availability
 
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Secluded Country Retreat, Near
Williams College & Outdoor Activities.
Williamstown, MA
Sleeps: 8
Bedrooms: 4
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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Charming Downtown Williamstown
Cottage - 5 Minute Walk to Campus.
Williamstown, MA
Sleeps: 7
Bedrooms: 3
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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A Home That Feels Like a Resort,
Situated In 3 Private Acres.
Williamstown, MA
Sleeps: 12
Bedrooms: 4
Bathrooms: 3.5
No Pets
Vacation Rental Rates & Availability
 
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Chic Williamstown Dollhouse. Quaint
Renovated Home In The Berkshires!
Williamstown, MA
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
No Pets
Vacation Rental Rates & Availability
 
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Relax In This 3 Bedroom House
Minutes From Williams College.
Williamstown, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 1
Pets Considered
Vacation Rental Rates & Availability
 
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Pet Friendly Country Home, Minutes
To Clark Art, Mass MoCA & College.
Williamstown, MA
Sleeps: 7
Bedrooms: 3
Bathrooms: 1.5
Pets Considered
Vacation Rental Rates & Availability
 
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Charming Stone Cottage - Walk To
Downtown Williamstown and College.
Williamstown, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 1
No Pets
Vacation Rental Rates & Availability
 
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Beautiful Pond & Mountain View In
The Berkshires, Williamstown MA.
Williamstown, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 1.5
No Pets
Vacation Rental Rates & Availability
 
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Large, Family-Friendly Farmhouse
Located In The Beautiful Berkshires.
Williamstown, MA
Sleeps: 13
Bedrooms: 6
Bathrooms: 2.5
No Pets
Vacation Rental Rates & Availability
 
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2000+ Guests Have Enjoyed This
Home. It's A "Good Time" Home.
Williamstown, MA
Sleeps: 16
Bedrooms: 5
Bathrooms: 3
Pets Considered
Vacation Rental Rates & Availability
 
 
 
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