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Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Rental types Garden Clothes dryer

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Price per night from

$251

Babbling Brook Retreat

Lakeville apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$264

Taghkanic House Modern Architectural Masterpiece

Taghkanic villa

  • 7 bedrooms
  • 10 bathrooms
  • sleeps 15

Responds fast! avg. 1 hour 20 minutes

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Price per night from

$5,725

Casa Campagna

Rhinebeck house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$298

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.

Match: Rental types Garden Clothes dryer

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Price per night from

$298

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

Beautiful House in Downtown Hudson, NY

Hudson house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$1,432

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Beautiful & Comfortable 4 bed 2 bath in Hudson, NY

Hudson house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 3 match: Clothes dryer, Garden, Rental types

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Price per night from

$630

Charming, modernized 1810 Farmhouse perfectly located in Hillsdale, NY

Hillsdale house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Clothes dryer, Garden, Rental types

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Price per night from

$344

Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi

Ghent house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 3 match: Clothes dryer, Garden, Rental types

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Price per night from

$228

Historic Gem Near Hudson, NY

Stuyvesant house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 3

1 of 3 match: Clothes dryer, Garden, Rental types

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Price per night from

$338

Hudson Valley Berkshires Cottage

Spencertown house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Clothes dryer, Garden, Rental types

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Price per night from

$196

Modern Glass House

Taghkanic house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 20 minutes

1 of 3 match: Clothes dryer, Garden, Rental types

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Price per night from

$516

Hillhouse Log Cabin

Hillsdale log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 13

“rest,relax,recharge” It's a Beautiful home that has all the modern conveniences. It's quiet, quaint and had just what I needed to get away from it all. I enjoyed morning coffee on the back deck among the trees and afternoon walks in the woods. A perfect place to recharge.

1 of 3 match: Rental types, Garden, Clothes dryer

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Price per night from

$487

Newly Renovated Lakefront Getaway on Robinson Pond

Copake house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 3 match: Clothes dryer, Garden, Rental types

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Price per night from

$287

Federal house on Armory Square

Hudson house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 3 match: Clothes dryer, Garden, Rental types

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Price per night from

$1,145

Hudson Haven

Hudson house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Clothes dryer, Garden, Rental types

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Price per night from

$258

Bassinova-on-Hudson

Coxsackie villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 43 minutes

1 of 3 match: Rental types, Garden, Clothes dryer

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Price per night from

$2,863

Newly Renovated Colonial on the River! Sleeps 5-6

Stockbridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 3 match: Garden, Rental types, Clothes dryer

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Price per night from

$327

Twin Island Lake House

Pine Plains house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Garden, Rental types, Clothes dryer

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Price per night from

$411

Modern Cozy Wooded Retreat

Spencertown house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Garden, Rental types, Clothes dryer

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Price per night from

$153

Escape to Avalon Cottage in the Hudson Valley

Craryville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Garden, Rental types, Clothes dryer

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Price per night from

$344

Chalet near 4 ski resorts with hot tub

East Chatham house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Garden, Rental types, Clothes dryer

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Price per night from

$1,030

CHALET-STYLE STUNNER ON A COUNTRY ROAD

Hillsdale house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Garden, Rental types, Clothes dryer

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Price per night from

$281

Roaring Rapids Cottage

Columbiaville house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 3 match: Garden, Rental types, Clothes dryer

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Price per night from

$287

Beautifully decorated & immaculate log chalet

Hillsdale log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 45 minutes

1 of 3 match: Rental types, Garden, Clothes dryer

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Price per night from

$229

The Cottage at Great Falls

Falls Village cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Perfect getaway location with all the amenities” Perfect getaway location with all the amenities – including a fireplace for a perfect winter stay. The cottage was clean and inviting, and the character of the furnishings and layout were incredible. Whether you want to stay in or venture out to nearby stores and restaurants, the cottage really is a perfect location for a vacation escape.

1 of 3 match: Rental types, Garden, Clothes dryer

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Price per night from

$275

Total Privacy! Tanglewood Retreat With Berkshire Views!

Hillsdale house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

1 of 3 match: Clothes dryer, Garden, Rental types

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Price per night from

$1,145

The FarmHouse

Millerton house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 3 match: Clothes dryer, Garden, Rental types

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Price per night from

$287

Lake House

Lakeville house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 9

Responds fast! avg. 2 hours 27 minutes

1 of 3 match: Clothes dryer, Garden, Rental types

1 of 3 filters match

Price per night from

$687

Spacious Contemporary With Beautiful Gardens

Housatonic house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 3 match: Clothes dryer, Garden, Rental types

1 of 3 filters match

Price per night from

$682

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