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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Dream Land 10 Minutes From Town
2 Story Berkshire Farmhouse.
Alford, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Private, Yet Close To Town.
2 Bedroom, 2 Bath, Large Deck.
Alford, MA
Sleeps: 6
Bedrooms: 2
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Charming Upscale County Cottage
In The Southern Berkshires.
Alford, MA
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
No Pets
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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Beautiful 7 Bedroom, 4.5 Bath
Berkshire Farm House, 160+ Acres.
Alford, MA
Sleeps: 16
Bedrooms: 7
Bathrooms: 4.5
Pets Considered
Vacation Rental Rates & Availability
 
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Private Lake Cottage Near Jacob’s
Pillow And Tanglewood.
Becket, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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Serene, Private Waterfront House,
Perfect Summer Retreat!
Becket, MA
Sleeps: 6
Bedrooms: 2
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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Berkshires Private Large Lakefront
Home On Robin Hood Lake.
Becket, MA
Sleeps: 10
Bedrooms: 6
Bathrooms: 3
Pets Considered
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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NEW Secluded A-Frame Cabin:
Fire Pit, Walk to Lake.
Becket, MA
Sleeps: 6
Bedrooms: 2
Bathrooms: 1
No Pets
Vacation Rental Rates & Availability
 
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Luxurious, Elegant 4 Acre
Berkshire/Pioneer Valley Retreat Pool.
Becket, MA
Sleeps: 10
Bedrooms: 5
Bathrooms: 4
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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Scenic Byway Waterfront Property
4,600 Sq. Ft. Sleeps 11.
Becket, MA
Sleeps: 11
Bedrooms: 3
Bathrooms: 2.5
Pets Considered
Vacation Rental Rates & Availability
 
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Berkshires Home on 11 Acres
With Pond & 2 Fire Pits!
Becket, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 3
No  Pets
Vacation Rental Rates & Availability
 
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Craftsman 2 BR, 2 BA Timber-Framed
Home In The Berkshire Forest.
Becket, MA
Sleeps: 6
Bedrooms: 2
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
Charming House With Large Porch
Near Jacob's Pillow
Becket, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 3
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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Lakefront 2 Bedroom Cottage In The
Berkshires In Western Massachusetts.
Becket, MA
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
Pets Considered
Vacation Rental Rates & Availability
 
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Becket Contemporary Cottage In The
Woods, Private Spring Fed Pond.
Becket, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 3
No Pets
Vacation Rental Rates & Availability
 
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3 Bedroom Berkshire House Rental
Perfect For Families Or Groups.
Becket, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 1
Pets Considered
Vacation Rental Rates & Availability
 
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Sunny, Stylish Berkshire Mountain
Retreat Near Jacob's Pillow.
Becket, MA
Sleeps: 8
Bedrooms: 4
Bathrooms: 2
Pets Considered
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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Private Lakefront Beach Property On
Goose Pond Near Tanglewood.
Becket, MA
Sleeps: 5
Bedrooms: 1
Bathrooms: 1
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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Beautiful Home With All Amenities,
Close To Everything. Fiber Optics.
Egremont, MA
Sleeps: 4
Bedrooms: 2
Bathrooms: 2
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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Timberdoodle, Peaceful And Tranquil Mountainside Tree House.
Egremont, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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Premier Waterfront Home With 2
Paddle Boards, 2 Kayaks, And Dock.
Egremont, MA
Sleeps: 8
Bedrooms: 2
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Farmhouse From A Magazine
3 Bedroom Heated Pool & Central Air.
Egremont, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 3.5
Pets Considered
Vacation Rental Rates & Availability
 
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Across From Catamount,
Newly 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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Manor Lane - Private Berkshire Estate One of a Kind French Manor House.
Great Barrington, MA
Sleeps: 12
Bedrooms: 4
Bathrooms: 4
Pets Considered
Vacation Rental Rates & Availability
 
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A Fun Farmhouse For All.
4 Bedroom, 3 Bath, Heated Pool.
Great Barrington, MA
Sleeps: 8
Bedrooms: 4
Bathrooms: 3
No Pets
Vacation Rental Rates & Availability
 
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Just You, The Frozen Lake, And 2
Nearby Ski Areas! Perfect Getaway.
Great Barrington, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 1
No Pets
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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Nestled Minutes From Main
Street, Great Barrington
Great Barrington, MA
Sleeps: 2
Bedrooms: 1
Bathrooms: 1
No Pets
Vacation Rental Rates & Availability
 
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Downtown GB Apartment Walk To
Shops And Restaurants.
Great Barrington, MA
Sleeps: 5
Bedrooms: 2
Bathrooms: 1
No Pets
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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Barn Apartment In Gorgeous
Stonybrook Farm In The Berkshires.
Great Barrington, MA
Sleeps: 2
Bedrooms: 1
Bathrooms: 1
No Pets
Vacation Rental Rates & Availability
 
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Beautiful 1920's Colonial 20
Minutes From Tanglewood
Great Barrington, MA
Sleeps: 8
Bedrooms: 4
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
Romantic Berkshires Cottage,
Stunning Views, Pool
Great Barrington, MA
Sleeps: 3
Bedrooms: 1
Bathrooms: 1
Pets Considered
Vacation Rental Rates & Availability
 
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4 Bedroom Family Vacation Home
In Great Barrington.
Great Barrington, MA
Sleeps: 9
Bedrooms: 4
Bathrooms: 3
Pets Considered
Vacation Rental Rates & Availability
 
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Modern Victorian On The Hill,
Easy walk to Main Street and Lake.
Great Barrington, MA
Sleeps: 10
Bedrooms: 4
Bathrooms: 3
Pets Considered
Vacation Rental Rates & Availability
 
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New Secluded 3 Bedroom Country Castle On 3+ Acres.
Great Barrington, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 3
No Pets
Vacation Rental Rates & Availability
 
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Twin Maple Farm:
Charming Modern Farmhouse.
Great Barrington, MA
Sleeps: 8
Bedrooms: 4
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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The Perfect Getaway On 3 Acres:
5 Bedroom, 3 Baths, Sleeps 12.
Great Barrington, MA
Sleeps: 12
Bedrooms: 5
Bathrooms: 3
No Pets
Vacation Rental Rates & Availability
 
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Fabulous Great Barrington Apartment,
5 Minutes From Downtown GB.
Great Barrington, MA
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
No Pets
Vacation Rental Rates & Availability
 
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Private Estate! Pool, Tennis
Court, 5 Min To Town & Ski Resorts
Great Barrington, MA
Sleeps: 12
Bedrooms: 4
Bathrooms: 4
Pets Considered
Vacation Rental Rates & Availability
 
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NEW House - The House On Round Pond, 4 BR, Stunning Water Views!
Great Barrington, MA
Sleeps: 8
Bedrooms: 4
Bathrooms: 4
Pets Considered
Vacation Rental Rates & Availability
 
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Simply Elegant Log Home, 3 Minutes From Butternut! Recently Renovated!
Great Barrington, MA
Sleeps: 10
Bedrooms: 5
Bathrooms: 3
Pets Considered
Vacation Rental Rates & Availability
 
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Beautiful 1920's Colonial
20 Minutes From Tanglewood.
Great Barrington, MA
Sleeps: 8
Bedrooms: 4
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Stunning Modern 5 BR Victorian In
Highly Desirable Part Of Town.
Great Barrington, MA
Sleeps: 10
Bedrooms: 5
Bathrooms: 4.5
Pets Considered
Vacation Rental Rates & Availability
 
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Rustic Modern 4 Bedroom House
In Great Barrington Near Town.
Great Barrington, MA
Sleeps: 8
Bedrooms: 4
Bathrooms: 2.5
Pets Considered
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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Hancock Log Cabin Retreat:
2 Miles To Jiminy Peak!
Hancock, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
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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Berkshire Village Carriage House,
Newly Built On 40 Acres.
Lanesborough, MA
Sleeps: 2
Bedrooms: 1
Bathrooms: 1
No Pets
Vacation Rental Rates & Availability
 
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Stunning Private Suite In The Beautiful Berkshires Near Jiminy Peak.
Lanesboro, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
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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Perfect House For Large Families Or Two Families To Share, Jiminy Peak.
Lanesboro, MA
Sleeps: 12
Bedrooms: 4
Bathrooms: 3
No Pets
Vacation Rental Rates & Availability
 
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Mountain Getaway In The
Heart Of The Berkshires!
Lanesboro, MA
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets
Vacation Rental Rates & Availability
 
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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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Monthly/Yearly, All Season Vacation
Rental, Minutes From Jimney Peak!
Lanesboro, MA
Sleeps: 4
Bedrooms: 2
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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Renovated Village Apt. In Gorgeous Victorian 10 Minutes To Tanglewood.
Lee, MA
 Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets
Vacation Rental Rates & Availability
 
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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
Vacation Rental Rates & Availability
 
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Tanglewood, Downtown Lenox, Lee,
Stockbridge 5 Minutes Or Less.
Lee, MA
Sleeps: 15
Bedrooms: 5
Bathrooms: 3.5
No Pets
Vacation Rental Rates & Availability
 
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Spacious Comfortable Charming
Family Farmhouse Great Location.
Lee, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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Modern And Spacious Berkshires Retreat - 5 Bedrooms & 3 Baths.
Lee, MA
Sleeps: 10
Bedrooms: 5
Bathrooms: 3
No Pets
Vacation Rental Rates & Availability
 
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Elegant 19th Cent. New England 2BR
Vacation Rental at Garfield House!
Lee, MA
Sleeps: 6
Bedrooms: 2
Bathrooms: 1.5
Pets Considered
Vacation Rental Rates & Availability
 
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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
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2 BR Newly Renovated Townehouse, Beautifully Decorated, Garfield House.
Lee, MA
Sleeps: 6
Bedrooms: 2
Bathrooms: 1.5
Pets Considered
Vacation Rental Rates & Availability
 
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Heart of Lenox!!
Renovated Downtown Apartment!
Lenox, MA
Sleeps: 6
Bedrooms: 2
Bathrooms: 1
No Pets
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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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Lenox - 4 Bedroom, 2.5 Bath
In Downtown Neighborhood.
Lenox, MA
Sleeps: 6
Bedrooms: 4
Bathrooms: 2.5
No Pets
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Enjoy comfortable elegance in this
secluded grand home located in Lenox.
Lenox, MA
Sleeps: 9
Bedrooms: 5
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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Newly Renovated 3 Bedroom House
In Lenox, Modern Interior Design!
Lenox, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
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Berkshire Estate In Heart Of Lenox,
10 BR, 9 1/2 BA, Walk-To-Town.
Lenox, MA
Sleeps: 17
Bedrooms: 10
Bathrooms: 9.5
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 House Close To Downtown,
Quiet Neighborhood, Dead End Street.
Lenox, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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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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1 Bedroom Located In The Heart Of
Historical Downtown Lenox.
Lenox, MA
Sleeps: 2
Bedrooms: 1
Bathrooms: 1
No Pets
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NEW! Cozy Lenox Home,
1.5 Mi. To Tanglewood Music!
Lenox, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 2.5
No Pets
Vacation Rental Rates & Availability
 
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Lemon Cottage Walk to Town/Tanglewood.
Lenox, MA
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
No Pets
Vacation Rental Rates & Availability
 
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Large Immaculate Home, 10 Minute
Walk To Lenox Center.
Lenox, MA
Sleeps: 8
Bedrooms: 4
Bathrooms: 3.5
Pets Considered
Vacation Rental Rates & Availability
 
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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
Vacation Rental Rates & Availability
 
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Blissful Summer.....Walking
Distance To Downtown Lenox
Lenox, MA
Sleeps: 5
Bedrooms: 3
Bathrooms: 1.5
No Pets
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Lenox Private Setting, Close To Tanglewood Rents Only By The Month.
Lenox, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
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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3 Bedroom, 1.5 Bath, Home Away
From Home With Beautiful Backyard.
Lenox, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 1
Pets Considered
Vacation Rental Rates & Availability
 
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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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Beautiful Berkshire Family Home, 5 Bedrooms, 3 Bathrooms, Sleeps 12+
Monterey, MA
Sleeps: 12
Bedrooms: 5
Bathrooms: 2.5
Pets Considered
Vacation Rental Rates & Availability
 
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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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NEW! Monterey Home With Porch
By Beach & State Parks!
Monterey, MA
Sleeps: 7
Bedrooms: 3
Bathrooms: 2.5
Pets Considered
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Private Cozy Retreat With Magic View, 3BR/2BA + Lower Level, Sleeps 10+
Monterey, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
No Pets
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Jaw Dropping Mountain & Lake Views
In This Stylish Mountain Home.
Monterey, MA
Sleeps: 8
Bedrooms: 4
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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Beautiful 3 Bedroom 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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Lakefront Berkshire Rental, Lake
Garfield: Private Dock, Boats, more.
Monterey, MA
Sleeps: 8
Bedrooms: 5
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Spacious Lakeside Berkshire Home Close To Tanglewood & Jacob's Pillow.
Monterey, MA
Sleeps: 12
Bedrooms: 4
Bathrooms: 4.5
No Pets
Vacation Rental Rates & Availability
 
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Cozy Monterey Family Chalet, Minutes
From Lake & 10 Minutes Butternut!
Monterey, MA
Sleeps: 6
Bedrooms: 2
Bathrooms: 1
Pets Considered
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
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Pleasant On Pleasant, Modern
Conveniences And Fresh Decor.
North Adams, MA
Sleeps: 7
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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4BR Berkshire Lakefront/Ski House,
Fully Fitted Kitchen. Hi Speed WiFi.
Otis, MA
Sleeps: 10
Bedrooms: 4
Bathrooms: 3
No Pets.
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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Beautiful Berkshire Home In Private
Community Of Otis Woodlands.
Otis, MA
Sleeps: 10
Bedrooms: 4
Bathrooms: 3
Pets Considered
Vacation Rental Rates & Availability
 
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Spacious Waterfront Berkshire Home,
Family Private Get-Away
Otis, MA
Sleeps: 8
Bedrooms: 4
Bathrooms: 3
No Pets
Vacation Rental Rates & Availability
 
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Charming 3 Bedroom Cedar Shingle
Lakefront Cottage.
Otis, MA
Sleeps: 7
Bedrooms: 3
Bathrooms: 1
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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Beautiful 3 BR Lakeside Log Home Close To All Berkshires Attractions.
Otis, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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Berkshire Vacation Home On
Hayden Pond 6 BR, 2 BA, Sleeps 10.
Otis, MA
Sleeps: 10
Bedrooms: 6
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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East Otis Reservoir Cabin With Porch, Walk to Lake!
Otis, MA
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
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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3BR/2BA Woodland Cottage,
Convenient, Private, Family Friendly.
Otis, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Private And Cozy In East Otis,
1 Bedroom, 1 Bathroom, Sleeps 4.
Otis, MA
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
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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Berkshire Pontoosuc Lake Beauty,
Brand New Construction On Lake.
Pittsfield, MA
Sleeps: 14
Bedrooms: 5
Bathrooms: 3.5
No Pets
Vacation Rental Rates & Availability
 
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Tranquil Lake House Getaway
On Onota Lake, 5BR, 2BA.
Pittsfield, MA
Sleeps: 11
Bedrooms: 5
Bathrooms: 2
No Pets
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
Vacation Rental Rates & Availability
 
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Newly Renovated 4 Bedroom
Lakefront House In The Berkshires.
Pittsfield, MA
Sleeps: 8
Bedrooms: 4
Bathrooms: 2.5
No Pets
Vacation Rental Rates & Availability
 
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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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Lake Front Home In Heart Of The
Berkshires Near Jiminy Peak.
Pittsfield, MA
Sleeps: 10
Bedrooms: 4
Bathrooms: 4
No Pets
Vacation Rental Rates & Availability
 
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Beautiful Log Cabin In The Woods, On
Pontoosuc Lake, Yet Near Everything.
Pittsfield, MA
Sleeps: 5
Bedrooms: 2
Bathrooms: 1.5
No Pets
Vacation Rental Rates & Availability
 
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Family Vacation Mountain
Lodge For All Seasons...
Pittsfield, MA
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets
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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Charming Berkshire Getaway
With Scenic Lake Views & Access
Pittsfield, MA
Sleeps: 4
Bedrooms: 2
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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Morning Face - Berkshire Estate
With Views And Privacy.
Richmond, MA
Sleeps: 10
Bedrooms: 4
Bathrooms: 4.5
No Pets
Vacation Rental Rates & Availability
 
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Secluded Berkshire Vacation Home
Near Tanglewood, A/C, Total Privacy.
Richmond, MA
Sleeps: 6
Bedrooms: 2
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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Magic Berkshires Retreat, Views,
3BR Farmhouse & 2BR Guesthouse.
Richmond, MA
Sleeps: 12
Bedrooms: 5
Bathrooms: 1
No Pets
Vacation Rental Rates & Availability
 
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Cabin w/3 Acres, Tennis + Basketball Courts By 4 Ski Mountains.
Sandisfield, MA
Sleeps: 12
Bedrooms: 4
Bathrooms: 3
Pets Considered
Vacation Rental Rates & Availability
 
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Sweet Dreams Retreat, Newly
Renovated Luxury Guest House.
Sandisfield, MA
Sleeps: 3
Bedrooms: 1
Bathrooms: 1
Pets Considered
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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Private Peninsula Surrounded By
Water, Minutes From Hiking & More!
Sheffield, MA
Sleeps: 9
Bedrooms: 3
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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The Little House In The Woods
Fresh, Cozy & Serene
Sheffield, MA
Sleeps: 6
Bedrooms: 2
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Grand Estate in Historic Stockbridge
9,000 Sq. Ft., Sleeps 12.
Stockbridge, MA
Sleeps: 12
Bedrooms: 6
Bathrooms: 6 Full, 2 Half
No Pets
Click Here For Rates & Availability
 
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Charming Stockbridge Historic
Victorian Near The Red Lion Inn.
Stockbridge, MA
Sleeps: 24
Bedrooms: 11
Bathrooms: 7.5
Pets Considered
Click Here For Rates & Availability
 
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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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Peaceful Woodland Home
In The Heart Of The Berkshires.
Stockbridge, MA
Sleeps: 8
Bedrooms: 3
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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Romantic Barn 3 Miles To Tanglewood,
1 Mile To Lake.
Stockbridge, MA
Sleeps: 8
Bedrooms: 4
Bathrooms: 2.5
No Pets
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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Stockbridge Bowl Lake Community,
Exc. Location, Close To Everything!
Stockbridge, MA
Sleeps: 7
Bedrooms: 4
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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Cabin Fever In Stockbridge,
2 Bedroom Cabin Fully Remodeled.
Stockbridge, MA
Sleeps: 6
Bedrooms: 2
Bathrooms: 1
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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Tranquil Getaway In The Stockbridge
Woods - Central To It All.
Stockbridge, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Sophisticated & Comfortable Retreat
A+ Location, Modern Amenities.
Stockbridge, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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NEW! Cozy Berkshires Cabin,
Walk To Beach & Lake!
Stockbridge, MA
Sleeps: 6
Bedrooms: 2
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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Beautiful Farm House Near Family
Ski Mountains & Other Fun Activities.
Stockbridge, MA
Sleeps: 8
Bedrooms: 4
Bathrooms: 4
No Pets
Vacation Rental Rates & Availability
 
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STOCKBRIDGE One Of The Finest Homes & Best Locations...
Stockbridge, MA
Sleeps: 11
Bedrooms: 4
Bathrooms: 3
Pets Considered
Vacation Rental Rates & Availability
 
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A Charming Mid 1800's
Stockbridge Farmhouse
Stockbridge, MA
Sleeps: 4
Bedrooms: 4
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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Vacation In A 5 Bedroom, 2 Bath,
Berkshire Farmhouse.
Stockbridge, MA
Sleeps: 15
Bedrooms: 5
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Completely Renovated Historic Home
In The Heart Of The Berkshires.
Stockbridge, MA
Sleeps: 6
Bedrooms: 2
Bathrooms: 2.5
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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Spectacular Housatonic River View
From Newly Renovated Cottage.
Stockbridge, MA
Sleeps: 4
Bedrooms: 2
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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Renovated Colonial on the River!
Fantastic Views.
Stockbridge, MA
Sleeps: 5
Bedrooms: 3
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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Charming Farmhouse Steps From
Downtown West Stockbridge.
West Stockbridge, MA
Sleeps: 5
Bedrooms: 2
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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4 Bedroom Home, Beautiful Gardens,
On Pond, Walking Distance To Town.
West Stockbridge, MA
Sleeps: 10
Bedrooms: 4
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability
 
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Newly Renovated 1910 Farmhouse,
Walk To Town, Perfect Retreat.
West Stockbridge, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 2.5
Pets Considered
Vacation Rental Rates & Availability
 
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Vacation In A Berkshire Farmhouse,
5 Bedrooms, 2 Baths, Sleeps 11-15.
West Stockbridge, MA
Sleeps: 15
Bedrooms: 5
Bathrooms: 2
Pets Considered
Vacation Rental Rates & Availability
 
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Newly Renovated 1910
Farmhouse Walk To Town
West Stockbridge, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 3
No Pets
Vacation Rental Rates & Availability
 
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Gorgeous Home, Nature Lover's
Delight In The Heart Of The Berkshires.
West Stockbridge, MA
Sleeps: 8
Bedrooms: 3
Bathrooms: 3.5
No Pets
Vacation Rental Rates & Availability
 
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Comfortable Home In The Heart Of Williamstown, Stroll To Spring Street.
Williamstown, MA
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
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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11 Acre Mid-Century Estate,
Newly Renovated.
Williamstown, MA
Sleeps: 8
Bedrooms: 4
Bathrooms: 3.5
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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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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Getaway @ The Patricia House
Where Adventures Await You
Williamstown, MA
Sleeps: 5
Bedrooms: 4
Bathrooms: 2
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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Huge Luxe Williamstown Updated
Victorian, Walk to Spring Street.
Williamstown, MA
Sleeps: 10
Bedrooms: 5
Bathrooms: 5.5
Pets Considered
Vacation Rental Rates & Availability
 
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Cozy Renovated Williamstown Cabin, Steps From Hiking Trails.
Williamstown, MA
Sleeps: 5
Bedrooms: 2
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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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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Vacation Getaway Or Remote
Work/School Location
Williamstown, MA
Sleeps: 7
Bedrooms: 4
Bathrooms: 2
No Pets
Vacation Rental Rates & Availability