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Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi

Ghent house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$227

Great rentals within 20 miles that match your search

Modern Cozy Wooded Retreat

Spencertown house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$152

Leisure home with beach front property

Coxsackie house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 25

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Price per night from

$2,567

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

$326

Newly Renovated Lakefront Getaway on Robinson Pond

Copake house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$286

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

$297

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

The Meadow House 4 bdrm 4 bath house

Stephentown house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$719

Roaring Rapids Cottage

Columbiaville house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$286

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

$856

Fabulous Post & Beam Berkshire Rental

Monterey house

  • 2 bathrooms
  • sleeps 7

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Price per night from

$205

Total Privacy! Tanglewood Retreat With Berkshire Views!

Hillsdale house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

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Price per night from

$1,141

Lake House

Lee house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 9

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Price per night from

$815

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

$286

A Peaceful Escape

Leeds house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 42 minutes

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Price per night from

$109

Federal house on Armory Square

Hudson house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$1,141

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

$343

Historic Gem Near Hudson, NY

Stuyvesant house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 3

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Price per night from

$337

Hudson Valley Berkshires Cottage

Spencertown house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$195

Mrs. Pleasant’s Plant Based B + B

Athens house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$198

Chalet near 4 ski resorts with hot tub

East Chatham house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$1,026

CHALET-STYLE STUNNER ON A COUNTRY ROAD

Hillsdale house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$280

Catskills Lake Retreat - Pool, hot tub, fire pit

Athens house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

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Price per night from

$400

Quite stay in the country

Nassau house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$297

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

$343

Private Village Home in Catskill Splendor

Catskill house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$571

Elevated Catskills Retreat: Hudson Valley Views

Catskill house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$451

Beautiful House in Downtown Hudson, NY

Hudson house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$1,426

Spacious Contemporary With Beautiful Gardens

Housatonic house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$679

Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$250

Escape to Avalon Cottage in the Hudson Valley

Craryville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$343

Modern Glass House

Taghkanic house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 20 minutes

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Price per night from

$514

Hudson Haven

Hudson house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$257

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

$799

Beautiful & Comfortable 4 bed 2 bath in Hudson, NY

Hudson house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$628

Beautiful Berkshires Historic Lenox Home

Lenox house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$172

Cozy Catskill Cabin

Catskill house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$256

** Private Berkshire Escape** Monthly Pricing Available

Lee house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$659

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