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39 Houses

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Newly Renovated Lakefront Getaway on Robinson Pond

Copake house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$286

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

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

Iris Room

Stockbridge farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$172

Horse Room

Stockbridge farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$172

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

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

$229

Charming 2+2 Lakeside Cottage on Best Lake in CT

Salisbury cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$206

OUR LOVELY VACATION HOME IS LOCATED IN THE CATSKIL

Catskill finca

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 52 minutes

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Price per night from

$571

Federal house on Armory Square

Hudson house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$1,141

Exclusive Rental in Beautiful Amenia!

Amenia house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$152

Spacious Lakeside Berkshire Home

Monterey house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$571

Hudson Valley Berkshires Cottage

Spencertown house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$195

Babbling Brook Retreat

Lakeville apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$263

Mrs. Pleasant’s Plant Based B + B

Athens house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$198

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

Close to attractions in the Berkshires

South Lee hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$114

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

Beautiful House in Downtown Hudson, NY

Hudson house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$1,426

Bassinova-on-Hudson

Coxsackie villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 43 minutes

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Price per night from

$2,852

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

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

Berkshires: Romantic Cottage with spectacular view

Great Barrington cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

“A Real Gem!!!” This cottage is the perfect place for two people. It is truly as beautiful as the pictures! The pool and grounds are exceptional and the view is breathtaking. The place is extremely well maintained and the owner is very kind and helpful. We had a fabulous weekend here and would gladly return!

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$273

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

$5,704

Quiet and peaceful cape cod on rural lake setting!

Rhinebeck house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$570

Casa Campagna

Rhinebeck house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$297

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

Cozy Catskill Cabin

Catskill house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$256

Holiday Inn Club Vacations Oak N' Spruce 2br suite Friday check-ins

South Lee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$70

Holiday Inn Club Vacations Oak N' Spruce 2BR Suite SATURDAY Check-Ins

South Lee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$81

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.

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Price per night from

$487

Modern, Private on 40 Acres New Renovation

Ashley Falls house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

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Price per night from

$915

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

** 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

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