Houses Spencertown

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Modern Cozy Wooded Retreat

Spencertown house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$153

Hudson Valley Berkshires Cottage

Spencertown house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$197

Great rentals within 20 miles that match your search

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

Total Privacy! Tanglewood Retreat With Berkshire Views!

Hillsdale house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

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Price per night from

$1,148

Lake House

Lee house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 9

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Price per night from

$820

Newly Renovated Lakefront Getaway on Robinson Pond

Copake house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$287

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

$299

Deluxe New Home, 2 Master Suites, Tanglewood Area

Lee house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$861

Eco-friendly cozy home in Gt. Barrington

Great Barrington house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$173

The Meadow House 4 bdrm 4 bath house

Stephentown house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$724

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

$861

Fabulous Post & Beam Berkshire Rental

Monterey house

  • 2 bathrooms
  • sleeps 7

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Price per night from

$206

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

Federal house on Armory Square

Hudson house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$1,148

Spacious Lakeside Berkshire Home

Monterey house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$574

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

$345

Historic Gem Near Hudson, NY

Stuyvesant house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 3

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Price per night from

$339

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

$1,032

Mrs. Pleasant’s Plant Based B + B

Athens house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$199

The Heart of Berkshires

Lee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$402

CHALET-STYLE STUNNER ON A COUNTRY ROAD

Hillsdale house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$281

Catskills Lake Retreat - Pool, hot tub, fire pit

Athens house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

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Price per night from

$402

Quite stay in the country

Nassau house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$299

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

$345

Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi

Ghent house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$229

Mountainside Getaway @ Jiminy Peak In the Berkshires

Hancock house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$568

Beautiful House in Downtown Hudson, NY

Hudson house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$1,434

Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$252

Roaring Rapids Cottage

Columbiaville house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$287

Leisure home with beach front property

Coxsackie house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 25

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Price per night from

$2,582

Spacious Contemporary With Beautiful Gardens

Housatonic house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$683

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

$797

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

$517

Hudson Haven

Hudson house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$259

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

Beautiful Berkshires Historic Lenox Home

Lenox house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$172

Escape to Avalon Cottage in the Hudson Valley

Craryville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$345

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

$631

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