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Houses Berkshires

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51 houses

Escape to the Berkshires!

Becket house

4 bedrooms / 3 bathrooms / sleeps 8

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$316

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

Private Guest House in Dtwn Lenox, Walk to Dining!

Lenox house

3 bedrooms / 3 bathrooms / sleeps 6

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$218

Beautiful Lakefront Berkshire Rental

Monterey house

5 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$637

Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house

4 bedrooms / 2 bathrooms / sleeps 10

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$251

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

Retreat in the Woods

Savoy house

2 bedrooms / 1 bathroom / sleeps 4

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$229

Spacious Lakeside Berkshire Home

Monterey house

4 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 2 hours 35 minutes

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Price per night from

$516

BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES

Otis house

6 bedrooms / 5 bathrooms / sleeps 14

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Price per night from

$687

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

Lake House

Lee house

5 bedrooms / 6 bathrooms / sleeps 9

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Price per night from

$817

Whitman Woods - A Berkshire Vacation

Hancock house

4 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$144

Fabulous Post & Beam Berkshire Rental

Monterey house

/ 2 bathrooms / sleeps 7

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$205

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

Heart of Lenox

Lenox house

2 bedrooms / 2 bathrooms / sleeps 4

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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

Responds fast! avg. 23 minutes

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$802

Tranquil 3BR Stockbridge House w/Private Deck

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 18 minutes

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$266

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

Deluxe New Home, 2 Master Suites, Tanglewood Area

Lee house

5 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 1 hour 25 minutes

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Price per night from

$861

Eco-friendly cozy home in Gt. Barrington

Great Barrington house

3 bedrooms / 2 bathrooms / sleeps 4

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$172

Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!

Becket house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$385

Berkshires Home w/Kayak - Walk to Stockbridge Bowl

Lenox house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$219

Golden Triangle in the Berkshires

Hancock house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$2,861

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Housatonic house

4 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 3 hours 18 minutes

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$219

Restored 1881 Farm House

Lenox house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 29 minutes

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Price per night from

$400

Renovated Lakefront House w/ Dock: Pets Welcome!

Monterey house

3 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$591

"Too Good" AKA 2 Goodrich St.

Stockbridge house

4 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 3 hours 29 minutes

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Price per night from

$572

The Gatehouse on Golden Hill

Lee house

4 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 3 hours 29 minutes

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Price per night from

$572

Hancock Log Cabin Retreat: 2 Miles to Jiminy Peak!

Hancock house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$208

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Lenox house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$255

Impeccable House Minutes from Downtown Great Barrington

Great Barrington house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 3 hours 29 minutes

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$572

Cozy Monterey Home w/ Porch: Walk to Lake Garfield

Monterey house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 18 minutes

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Price per night from

$213

Private Home Overlooking Stevens Lake

Great Barrington house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 29 minutes

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$516

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

NEW! Cozy Great Barrington Home 1 Mi to Ski Resort

Great Barrington house

4 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 3 hours 46 minutes

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Price per night from

$296

Fox Hollow Laurel Lake Ranch

Lenox house

4 bedrooms / 5 bathrooms / sleeps 11

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Price per night from

$572

** Private Berkshire Escape** Monthly Pricing Available

Lee house

4 bedrooms / 2 bathrooms / sleeps 12

Responds fast! avg. 3 hours 29 minutes

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Price per night from

$659

NEW! Peaceful Family Home w/ Fire Pit & Large Yard

Williamstown house

4 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$284

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