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Houses Berkshires

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age 0-16
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36 houses

Escape to the Berkshires!

Becket house

4 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$315

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Hinsdale house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$218

Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house

4 bedrooms / 2 bathrooms / sleeps 10

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Price per night from

$263

Spacious Lakeside Berkshire Home

Monterey house

4 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 2 hours 40 minutes

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$573

Quiet Comfortable Cabin 5 Min. Walk to Lake

Becket house

2 bedrooms / 1 bathroom / sleeps 4

“Great winter getaway spot” My girlfriend and I spent new years at this awesome cabin tucked away in Becket, ma. It was quiet, clean, spacious and just about everything we could have asked for. The property was great, there was lots to do in nearby areas and we had a great time spending nights by the wood stove watching movies on their entertainment setup. I'd definitely recommend it for anyone looking to get out of the city for a few days to just relax and do something different!

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$171

Gem of the Berkshires, walk to downtown & lake.

Great Barrington house

5 bedrooms / 4 bathrooms / sleeps 12

“Wonderful Home!” We had a wonderful weekend! The home and area are lovely - easy walk to town for drinks and dinner - and enjoyed sitting on the many porches, looking out at the view. The home has been upgraded and the kitchen and living areas are beautiful. Thank you!

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$344

Whitman Woods - A Berkshire Vacation

Hancock house

4 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$172

Retreat in the Woods

Savoy house

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$229

Fabulous Post & Beam Berkshire Rental

Monterey house

/ 2 bathrooms / sleeps 7

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Price per night from

$205

Lake House

Lee house

5 bedrooms / 6 bathrooms / sleeps 9

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Price per night from

$818

Berkshire Farmhouse Vacation

West Stockbridge house

5 bedrooms / 2 bathrooms / sleeps 15

“Quaint Getaway” We were 2 families with 5 kids staying for the weekend. We had plenty of space to spread out, cook & dine together and lots of bedroom options to meet everyone's needs. The house had a lot of antique charm like exposed beams in the living room and paneled walls in the dining room. We were there on a rainy, cold weekend, so did not have an opportunity to enjoy the grounds or porch, but imagine it would be lovely in the warmer weather. Elaine (and her shop) were on the same grounds and she was available for questions about the area. Overall a very relaxing & convenient experience.

Responds fast! avg. 47 minutes

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Price per night from

$298

Vacation Home on 10 Acres with Pool and Spa

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$859

Heart of Lenox

Lenox house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 44 minutes

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Price per night from

$287

One of the Finest Homes and Best location in the Berkshires

Stockbridge house

4 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$802

Eco-friendly cozy home in Gt. Barrington

Great Barrington house

3 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$172

Deluxe New Home, 2 Master Suites, Tanglewood Area

Lee house

5 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 1 hour 42 minutes

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Price per night from

$859

Golden Triangle in the Berkshires

Hancock house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$2,863

Restored 1881 Farm House

Lenox house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$400

The Gatehouse on Golden Hill

Lee house

4 bedrooms / 4 bathrooms / sleeps 12

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Price per night from

$744

"Too Good" AKA 2 Goodrich St.

Stockbridge house

4 bedrooms / 4 bathrooms / sleeps 12

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Price per night from

$629

Newly Renovated Colonial on the River! Sleeps 5-6

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 5

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Price per night from

$327

Fox Hollow Laurel Lake Ranch

Lenox house

4 bedrooms / 5 bathrooms / sleeps 11

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Price per night from

$573

** Private Berkshire Escape** Monthly Pricing Available

Lee house

4 bedrooms / 2 bathrooms / sleeps 12

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Price per night from

$659

Spacious Contemporary With Beautiful Gardens

Housatonic house

4 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$682

The Heart of Berkshires

Lee house

4 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$401

Private Berkshire County Retreat

Sheffield house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$457

6BR Berkshire Bliss - 38 private acres - close to skiing and town

Lanesborough house

6 bedrooms / 5 bathrooms / sleeps 15

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Price per night from

$795

Art House! Spacious Getaway By Mass Moca

North Adams house

6 bedrooms / 2 bathrooms / sleeps 12

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Price per night from

$458

Walk To Tanglewood, Stockbridge Bowl Lake, Wheatleigh

Stockbridge house

3 bedrooms / 5 bathrooms / sleeps 8

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Price per night from

$911

LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE

Lenox house

5 bedrooms / 3 bathrooms / sleeps 14

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Price per night from

$516

Great rentals within 20 miles that match your search

Flight's End-A Country Home with Babbling Brook

Hawley house

3 bedrooms / 2 bathrooms / sleeps 8

“Perfect getaway” We spent few days there. It is very quiet and private. We loved the retro look. Looking forward going there again. It was New Year's eve we were hoping for.

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$206

The Meadow House 4 bdrm 4 bath house

Stephentown house

4 bedrooms / 4 bathrooms / sleeps 12

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Price per night from

$722

Charming Affordable Home for groups up to 14

Shelburne Falls house

7 bedrooms / 3 bathrooms / sleeps 14

“Beautiful house in beautiful village!” Thank you for the use of your beautiful house. It was perfect for our wedding weekend. Everyone was very comfortable and had a great time. Looking forward to coming back again in the future.

Responds fast! avg. 3 hours 58 minutes

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Price per night from

$573

Rural Berkshires Home

Ashfield house

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$23

Berkshire house w/ fireplace, A/C, WiFi & laundry

Plainfield house

3 bedrooms / 2 bathrooms / sleeps 10

“Peaceful country home” Beautiful, welcoming home in a perfect location. Warm and inviting living room; bright, airy bedrooms.

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Price per night from

$234

Private Country home near Berkshires

Cherry Plain house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$98

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