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Total Privacy! Tanglewood Retreat With Berkshire Views!

Hillsdale house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

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Price per night from

$1,145

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

CHALET-STYLE STUNNER ON A COUNTRY ROAD

Hillsdale house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$281

Great rentals within 20 miles that match your search

Federal house on Armory Square

Hudson house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$1,144

Spacious Lakeside Berkshire Home

Monterey house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$572

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

Historic Gem Near Hudson, NY

Stuyvesant house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 3

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Price per night from

$338

Lake House

Lakeville house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 9

Responds fast! avg. 2 hours 27 minutes

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Price per night from

$687

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

$1,029

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

$198

Twin Island Lake House

Pine Plains house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$411

The Heart of Berkshires

Lee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$401

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 Village Home in Catskill Splendor

Catskill house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$572

Spacious Contemporary With Beautiful Gardens

Housatonic house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$680

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

Modern, Private on 40 Acres New Renovation

Ashley Falls house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

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Price per night from

$913

Beautiful Berkshires Historic Lenox Home

Lenox house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$172

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

$515

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

$629

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

$800

Hudson Haven

Hudson house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$257

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

Cozy Catskill Cabin

Catskill house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$256

Modern Cozy Wooded Retreat

Spencertown house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$153

Leisure home with beach front property

Coxsackie house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 25

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Price per night from

$2,577

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

** Private Berkshire Escape** Monthly Pricing Available

Lee house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$659

Private Berkshire County Retreat

Sheffield house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$686

Expansive Berkshire Property

Stockbridge house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$458

Private Home Overlooking Stevens Lake (31 Night Min)

Great Barrington house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$572

Restored 1881 Farm House

Lenox house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$572

The Gatehouse on Golden Hill

Lee house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$744

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

$298

Deluxe New Home, 2 Master Suites, Tanglewood Area

Lee house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$859

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

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