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!
Lee, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Garfield House Studio At 208,
Porch, Private Entrance.
Sleeps: 2
Bedrooms: Studio
Bathrooms: 1
Pets Welcome
Lee, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Relax Between Your Berkshire Adventures! Easy Walk To Town! Centrally Located!
Sleeps: 6
Bedrooms: 3
Bathrooms: 1
No Pets
Lee, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Enjoy Relaxing Organic Living In The
Heart of the Berkshires!
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Lee, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Tanglewood, Downtown Lenox, Lee,
Stockbridge 5 Minutes Or Less.
Sleeps: 15
Bedrooms: 5
Bathrooms: 3.5
No Pets
Lee, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Spacious Comfortable Charming
Family Farmhouse Great Location.
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
No Pets
Lee, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Modern And Spacious Berkshires
Retreat – 5 Bedrooms & 3 Baths.
Sleeps: 10
Bedrooms: 5
Bathrooms: 3
No Pets
Lee, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Elegant 19th Cent. New England 2BR
Vacation Rental at Garfield House!
Sleeps: 6
Bedrooms: 2
Bathrooms: 1.5
Pets Welcome
South Lee, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Spectacular Setting On Your Own
Private Lake Close To It All.
Sleeps: 10
Bedrooms: 4
Bathrooms: 3
Pets Welcome
Lee, MA
Southern Berkshire Area
Berkshire Vacation Rentals
2 BR Newly Renovated Townehouse,
Beautifully Decorated, Garfield House.
Sleeps: 6
Bedrooms: 2
Bathrooms: 1.5
Pets Welcome
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
Heart of Lenox!!
Renovated Downtown Apartment!
Sleeps: 6
Bedrooms: 2
Bathrooms: 1
No Pets
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
1898 Refurbished Farmhouse – Easy
Walk To Lenox Center.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2.5
Pets Welcome
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
Village View – Elegant, Comfortable,
Historic Home In Downtown Lenox.
Sleeps: 9
Bedrooms: 6
Bathrooms: 3
No Pets
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
Enjoy Comfortable Elegance In This
Secluded Grand Home In Lenox.
Sleeps: 9
Bedrooms: 5
Bathrooms: 2
No Pets
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
Unique Lenox Condo, Quiet
Neighborhood, Walk to Town.
Sleeps: 4
Bedrooms: 2
Bathrooms: 2
No Pets
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
Newly Renovated 3 Bedroom House
In Lenox, Modern Interior Design!
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
5 Star Casual Elegance For 5 Star
Guests, On Beautiful And Quiet Street.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2.5
No Pets
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
The Best Of Both Worlds, Country and
Culture In The Berkshires.
Sleeps: 8
Bedrooms: 5
Bathrooms: 3
No Pets
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
Lenox House Close To Downtown,
Quiet Neighborhood, Dead End Street.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
Lovely Home In Heart Of Lenox & Just
Minutes From Tanglewood By Car.
Sleeps: 4
Bedrooms: 2
Bathrooms: 2
No Pets
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
1 Bedroom Located In The Heart Of
Historical Downtown Lenox.
Sleeps: 2
Bedrooms: 1
Bathrooms: 1
No Pets
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
NEW! Cozy Lenox Home,
1.5 Mi. To Tanglewood Music!
Sleeps: 6
Bedrooms: 3
Bathrooms: 2.5
No Pets
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
Lemon Cottage Walk to
Town/Tanglewood.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
No Pets
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
Large Immaculate Home, 10 Minute
Walk To Lenox Center.
Sleeps: 8
Bedrooms: 4
Bathrooms: 3.5
Pets Welcome
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
51 Church Street, Lenox MA – One Bedroom Unit, Refined Getaway.
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
Luxury Berkshires Retreat, Main House & Studio, Unwind In The Berkshires.
Sleeps: 15
Bedrooms: 7
Bathrooms: 4.5
No Pets
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
Lenox Private Setting, Close To
Tanglewood Rents Only By The Month.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
Newly Renovated 3 BR Haus In Lenox
With Modern Interior Design.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
Heart Of Lenox Walk To Town Cozy Cottage! Perfect Location For Walking.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
No Pets
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
Lenox Waterfront Cottage – Tranquil
Escape, near Berkshire Attractions.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1.5
No Pets
Lenox, MA
Central Berkshire Area
Berkshire Vacation Rentals
5 STAR! Lenox Vacation Home.
Private, Luxury, Perfect Location.
Sleeps: 8
Bedrooms: 4
Bathrooms: 3.5
Pets Welcome
Monterey, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Peaceful, Newly Renovated Lakeside
Cottage On Lake Garfield – Berkshires.
Sleeps: 5
Bedrooms: 2
Bathrooms: 1
Pets Welcome
Monterey, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Cozy Monterey Family Chalet, Minutes From Lake & 10 Minutes From Butternut!
Sleeps: 6
Bedrooms: 2
Bathrooms: 1
Pets Welcome
Monterey, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Cozy Family Chalet, Minutes From
Lake & 10 Minutes From Butternut!
Sleeps: 6
Bedrooms: 2
Bathrooms: 1
Pets Welcome
Monterey, MA
Southern Berkshire Area
Berkshire Vacation Rentals
NEW! Monterey Home With Porch
By Beach & State Parks!
Sleeps: 7
Bedrooms: 3
Bathrooms: 2.5
Pets Welcome
Monterey, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Private Cozy Retreat With Magic View,
3BR/2BA + Lower Level, Sleeps 10+
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
No Pets
Monterey, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Jaw Dropping Mountain & Lake Views
In This Stylish Mountain Home.
Sleeps: 8
Bedrooms: 4
Bathrooms: 2
No Pets
Monterey, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Stay At Beaver Lodge! Enjoy The Country Views, Super Clean.
Sleeps: 2
Bedrooms: 1
Bathrooms: 1
Pets Welcome
Monterey, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Berkshire Lake House On Lake
Garfield, Monterey MA – 4 Bedrooms.
Sleeps: 10
Bedrooms: 4
Bathrooms: 3
Pets Welcome
Monterey, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Lakefront Berkshire Rental, Lake
Garfield: Private Dock, Boats, More.
Sleeps: 8
Bedrooms: 5
Bathrooms: 2
Pets Welcome
Monterey, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Gorgeous Log Cabin On
10 Wooded Acres In The Berkshires.
Sleeps: 9
Bedrooms: 3
Bathrooms: 3
No Pets
Monterey, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Spacious Lakeside Berkshire Home Close To Tanglewood And Jacob’s Pillow.
Sleeps: 12
Bedrooms: 4
Bathrooms: 4.5
No Pets
Monterey, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Cozy Lakeside Cottage Oasis, Tranquil Extension Of Lake Garfield.
Sleeps: 7
Bedrooms: 3
Bathrooms: 2.5
No Pets