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50 Houses

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nesteldown pet friendly

Old Chatham guest house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$459

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Price per night from

$1,260

Charming Guest Suite

Old Chatham apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$155

Great rentals within 20 miles that match your search

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

A Park View Apartment in Hudson

Hudson apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$230

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

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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Price per night from

$230

Roaring Rapids Cottage

Columbiaville house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$287

Lake House

Lee house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 9

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Price per night from

$819

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

West Coxsackie house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$287

Cozy basement Studio Apartment Albany,NY

Albany house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$102

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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Price per night from

$339

Federal house on Armory Square

Hudson house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$1,147

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

Hudson Valley Berkshires Cottage

Spencertown house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$196

Mrs. Pleasant’s Plant Based B + B

Athens house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$199

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

Elevated Catskills Retreat: Hudson Valley Views

Catskill house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$453

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

Quite stay in the country

Nassau house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$298

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

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

Mountainside Getaway @ Jiminy Peak In the Berkshires

Hancock house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$568

Albany Vacation Rental -2nd floor, 3 bedroom (AA guest House, Inn)

Albany apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

Responds fast! avg. 31 minutes

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Price per night from

$172

Private Country home near Berkshires

Cherry Plain house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$98

Bassinova-on-Hudson

Coxsackie villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 43 minutes

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Price per night from

$2,866

Beautiful House in Downtown Hudson, NY

Hudson house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$1,433

Albany Vacation Rental -Garden Apt, 2 bedrooms "AA guest House, Inn."

Albany apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 31 minutes

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Price per night from

$172

Beautiful Berkshires Historic Lenox Home

Lenox house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$172

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

$796

Hudson Haven

Hudson house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$258

The Mark on Maiden @ 37 Maiden Lane - 2 Bedroom Apartment + Workstation

Albany apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$98

NEWLY RENOVATED BEAUTIFUL HOME

Albany house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$207

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

$803

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rentals in Old Chatham

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