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23 Houses

Taghkanic House Modern Architectural Masterpiece

Taghkanic villa

  • 7 bedrooms
  • 10 bathrooms
  • sleeps 15

Responds fast! avg. 1 hour 20 minutes

Match: Garden Air conditioning Shared outdoor pool (unheated)

All filters match

Price per night from

$5,725

Eco-friendly cozy home in Gt. Barrington

Great Barrington house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Garden Air conditioning Shared outdoor pool (unheated)

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Price per night from

$172

Newly Renovated Lakefront Getaway on Robinson Pond

Copake house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

Match: Garden Air conditioning Shared outdoor pool (unheated)

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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.

Match: Garden Air conditioning Shared outdoor pool (unheated)

All filters match

Price per night from

$298

Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Garden Air conditioning Shared outdoor pool (unheated)

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Price per night from

$251

Modern Glass House

Taghkanic house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 20 minutes

Match: Garden Air conditioning Shared outdoor pool (unheated)

All filters match

Price per night from

$516

These homes match some but not all of your filters. Clear all filters

Charming, modernized 1810 Farmhouse perfectly located in Hillsdale, NY

Hillsdale house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Garden, Shared outdoor pool (unheated), Air conditioning

1 of 3 filters match

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: Garden, Shared outdoor pool (unheated), Air conditioning

1 of 3 filters match

Price per night from

$228

Beautiful & Comfortable 4 bed 2 bath in Hudson, NY

Hudson house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 3 match: Garden, Shared outdoor pool (unheated), Air conditioning

1 of 3 filters match

Price per night from

$630

Historic Gem Near Hudson, NY

Stuyvesant house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 3

1 of 3 match: Garden, Shared outdoor pool (unheated), Air conditioning

1 of 3 filters match

Price per night from

$338

Hudson Valley Berkshires Cottage

Spencertown house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Garden, Shared outdoor pool (unheated), Air conditioning

1 of 3 filters match

Price per night from

$196

Babbling Brook Retreat

Lakeville apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Garden, Shared outdoor pool (unheated), Air conditioning

1 of 3 filters match

Price per night from

$264

Federal house on Armory Square

Hudson house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 3 match: Garden, Shared outdoor pool (unheated), Air conditioning

1 of 3 filters match

Price per night from

$1,145

Hudson Haven

Hudson house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Garden, Shared outdoor pool (unheated), Air conditioning

1 of 3 filters match

Price per night from

$258

Beautiful House in Downtown Hudson, NY

Hudson house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 3 match: Garden, Shared outdoor pool (unheated), Air conditioning

1 of 3 filters match

Price per night from

$1,432

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: Garden, Shared outdoor pool (unheated), Air conditioning

1 of 3 filters match

Price per night from

$487

Casa Campagna

Rhinebeck house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Garden, Shared outdoor pool (unheated), Air conditioning

1 of 3 filters match

Price per night from

$298

Bassinova-on-Hudson

Coxsackie villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 43 minutes

1 of 3 match: Garden, Shared outdoor pool (unheated), Air conditioning

1 of 3 filters match

Price per night from

$2,863

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!

1 of 3 match: Garden, Air conditioning, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$274

A Park View Apartment in Hudson

Hudson apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 3 match: Garden, Shared outdoor pool (unheated), Air conditioning

1 of 3 filters match

Price per night from

$229

Modern Cozy Wooded Retreat

Spencertown house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Garden, Shared outdoor pool (unheated), Air conditioning

1 of 3 filters match

Price per night from

$153

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: Garden, Shared outdoor pool (unheated), Air conditioning

1 of 3 filters match

Price per night from

$229

Roaring Rapids Cottage

Columbiaville house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 3 match: Garden, Shared outdoor pool (unheated), Air conditioning

1 of 3 filters match

Price per night from

$287

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