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Houses Berkshires

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50 houses

Escape to the Berkshires!

Becket house

4 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$314

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

Responds fast! avg. 3 hours 21 minutes

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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

$585

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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Price per night from

$171

Retreat in the Woods

Savoy house

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$229

Spacious Lakeside Berkshire Home

Monterey house

4 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 2 hours 22 minutes

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Price per night from

$523

BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES

Otis house

6 bedrooms / 5 bathrooms / sleeps 14

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Price per night from

$796

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

$948

Whitman Woods - A Berkshire Vacation

Hancock house

4 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$115

Fabulous Post & Beam Berkshire Rental

Monterey house

/ 2 bathrooms / sleeps 7

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Price per night from

$238

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.

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Price per night from

$296

Heart of Lenox

Lenox house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 28 minutes

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Price per night from

$170

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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Price per night from

$802

Tranquil 3BR Stockbridge House w/Private Deck

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 29 minutes

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$402

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

$937

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

$860

Eco-friendly cozy home in Gt. Barrington

Great Barrington house

3 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$186

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

Becket house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 0 minutes

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Price per night from

$480

Berkshires Home w/Kayak - Walk to Stockbridge Bowl

Lenox house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 0 minutes

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Price per night from

$243

Golden Triangle in the Berkshires

Hancock house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$3,314

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Housatonic house

4 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 3 hours 21 minutes

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Price per night from

$283

Restored 1881 Farm House

Lenox house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 1 minutes

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Price per night from

$515

Pet-Friendly Lakefront Home w/ Dock & Watercraft!

Monterey house

3 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 3 hours 21 minutes

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Price per night from

$827

"Too Good" AKA 2 Goodrich St.

Stockbridge house

4 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 3 hours 1 minutes

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Price per night from

$629

The Gatehouse on Golden Hill

Lee house

4 bedrooms / 4 bathrooms / sleeps 15

Responds fast! avg. 3 hours 1 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

Responds fast! avg. 3 hours 21 minutes

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Price per night from

$366

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Lenox house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 21 minutes

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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 1 minutes

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Price per night from

$572

Cozy Monterey Home w/ Porch: Walk to Lake Garfield

Monterey house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 29 minutes

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Price per night from

$231

Private Home Overlooking Stevens Lake

Great Barrington house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 1 minutes

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Price per night from

$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 21 minutes

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Price per night from

$315

NEW! Kid-Friendly & Views! Hike, Bike, Grill, Swim

Adams house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 21 minutes

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Price per night from

$315

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 1 minutes

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Price per night from

$659

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