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62 Houses

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nesteldown pet friendly

Old Chatham guest house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$458

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$1,260

Charming Guest Suite

Old Chatham apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$155

Great rentals within 20 miles that match your search

Iris Room

Stockbridge farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$172

Horse Room

Stockbridge farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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$172

Thanksgiving week lux condo/4 Berkshires

Williamstown condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$263

Berkshires Spacious Comfortable Charming Farmhouse

Lee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“lovely stay” The house is comfortable, clean, and convenient to Lenox, Stockbridge, and the rest of the Berkshires. Traffic from the street can be a bit loud at times, but it quiets down at night.

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$373

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

$298

Bentley/Wyndham Hancock Mass at Jiminy Peak

Hancock condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$430

Eco-friendly cozy home in Gt. Barrington

Great Barrington house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

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$172

Golden Triangle in the Berkshires

Hancock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$2,863

Beautifully decorated & immaculate log chalet

Hillsdale log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 45 minutes

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$229

Gartner House, a charming home in Lenox

Lenox apartment

  • 4 bedrooms
  • 1 bathroom
  • sleeps 7

“Great Location In Lenox” My family, friends, & I had a wonderful 2 weeks at Gartner House. It is within easy walking distance of nice shops, terrific restaurants, & a friendly library. Not far are Chesterwood, Tanglewood, Jacob's Pillow, Mass MoCa, Norman Rockwell, & a great, newly renovated Beshire Museum in Pittsfield.

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$229

Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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$251

The Meadow House 4 bdrm 4 bath house

Stephentown house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

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$722

Lake House

Lee house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 9

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$818

Modern Cozy Wooded Retreat

Spencertown house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$153

Leisure home with beach front property

Coxsackie house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 25

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$2,577

Newly Renovated Colonial on the River! Sleeps 5-6

Stockbridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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$327

Cozy basement Studio Apartment Albany,NY

Albany house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$102

Beautiful 52 Acre Farmhouse- weekly discounted rates - please inquire.

West Coxsackie house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$287

Federal house on Armory Square

Hudson house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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$1,145

Heart of Lenox

Lenox house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 12 minutes

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Price per night from

$344

Whitman Woods - A Berkshire Vacation

Hancock house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$172

Historic Gem Near Hudson, NY

Stuyvesant house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 3

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$338

Bassinova-on-Hudson

Coxsackie villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 43 minutes

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Price per night from

$2,863

Hudson Valley Berkshires Cottage

Spencertown house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$196

Mrs. Pleasant’s Plant Based B + B

Athens house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$198

A Park View Apartment in Hudson

Hudson apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$229

UMIQUE Country Condo, 1BR 1 BA - NEW

Hancock condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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Price per night from

$260

Private room in house. Albany Medical/colleges and Downtown Albany.

Albany house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$63

Private room in house. Albany Medical/colleges and Downtown Albany.

Albany house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$63

Quite stay in the country

Nassau house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$298

Charming, modernized 1810 Farmhouse perfectly located in Hillsdale, NY

Hillsdale house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$344

Close to attractions in the Berkshires

South Lee hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$115

Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi

Ghent house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$228

Holiday Inn Club Vacations Oak N' Spruce 2br suite Friday check-ins

South Lee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$70

Holiday Inn Club Vacations Oak N' Spruce 2BR Suite SATURDAY Check-Ins

South Lee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$71

Viewing 38 of 62
rentals in Old Chatham

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