Houses Vermont

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599 houses

Private Berkshire County Retreat

Sheffield house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Rental types Private outdoor pool (unheated) Smoking allowed

All filters match

Price per night from

$686

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Relax at our East Hampton home

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Smoking allowed, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$902

Charming cottage in the heart of East Hampton village

East Hampton house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Smoking allowed, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$382

Full Basement unit with gorgeous view.

Salem house

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

2 of 3 match: Smoking allowed, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$172

Wine Country Retreat w/ Dock & Pool on Mattituck Inlet

Mattituck house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

2 of 3 match: Smoking allowed, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$430

Idyllic North Fork Waterfront Home with Pool

Mattituck house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

2 of 3 match: Smoking allowed, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$430

Summer Shangri La on Sag Harbor Memorial Day to Labor Day!!

Noyack house

  • 5 bedrooms
  • 8 bathrooms
  • sleeps 10

2 of 3 match: Private outdoor pool (unheated), Rental types, Smoking allowed

2 of 3 filters match

Price per night from

$1,530

The Gatehouse on Golden Hill

Lee house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

2 of 3 match: Private outdoor pool (unheated), Rental types, Smoking allowed

2 of 3 filters match

Price per night from

$744

Expansive Berkshire Property

Stockbridge house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 3 match: Private outdoor pool (unheated), Rental types, Smoking allowed

2 of 3 filters match

Price per night from

$458

Modern 3BR 2BA Home w/ Patio & Outdoor Salt Pool

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Smoking allowed, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$343

2 of 3 match: Private outdoor pool (unheated), Rental types, Smoking allowed

2 of 3 filters match

Price per night from

$764

Serene & Private East Hampton Summer Rental w/pool

East Hampton house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Smoking allowed, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$984

Modern North Fork Haven: Beachfront,Private Pool

Southold house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

Responds fast! avg. 2 hours 17 minutes

2 of 3 match: Smoking allowed, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$842

Coastal Haven: Private Pool, Bay Access, Water Sports

Aquebogue house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 17 minutes

2 of 3 match: Smoking allowed, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$351

2 of 3 match: Smoking allowed, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$268

Very Private and Tranquil House in wooded estate.

Southampton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Smoking allowed, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$1,148

Abigail ‘s Nest

Brimfield house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 14

2 of 3 match: Smoking allowed, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$1,033

** Private Berkshire Escape** Monthly Pricing Available

Lee house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

2 of 3 match: Smoking allowed, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$659

Classic Southampton Home: 5BR, Pool,Jacuzzi, Cooper's Beach

Southampton house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 17 minutes

2 of 3 match: Smoking allowed, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$930

Stylish Sunset Retreat: Near Beach, Pool, Hot Tub

Wading River house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 17 minutes

2 of 3 match: Smoking allowed, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$424

Sweet Retreat: Private Pool, Outdoor Jacuzzi, Coopers Beach

Southampton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 17 minutes

2 of 3 match: Smoking allowed, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$470

Silver Beach Bliss: Luxury Waterfront Home w/ Pool

Baiting Hollow house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 17 minutes

2 of 3 match: Smoking allowed, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$736

Respite Ranch: Private Pool, Hot Tub, Beach Access

Mattituck house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 17 minutes

2 of 3 match: Smoking allowed, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$332

Sprawling Southampton Home: Private Pool, Hot tub, Game Room

Southampton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 13

Responds fast! avg. 2 hours 17 minutes

2 of 3 match: Smoking allowed, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$699

Southampton Retreat: Heated Pool, Hot Tub, Near Beach

Southampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 17 minutes

2 of 3 match: Smoking allowed, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$418

Roanoke Ranch Home: 3BR, Private Pool, Hot Tub, North Fork

Riverhead house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 17 minutes

2 of 3 match: Smoking allowed, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$369

Redding Relaxation Haven - Tranquil Home with Pool, Gardens Galore

Redding house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Smoking allowed, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$729

Cozy Moose Log Cabin - Pool, Trails, Secluded Retreat

Newtown house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 3 match: Smoking allowed, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$409

Elegant Newtown Getaway - High-End Amenities, Infinity Pool, Media Room

Newtown house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 6

2 of 3 match: Smoking allowed, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$719

2 of 3 match: Smoking allowed, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$320

Bayso By The Bay

Freeport apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 3 match: Rental types, Private outdoor pool (unheated), Smoking allowed

1 of 3 filters match

Price per night from

$368

Lushly Landscaped Contemporary With Pool East Hampton North

East Hampton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Smoking allowed, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$574

Spectacular Family Resort in Hampton Bays, NY

Hampton Bays house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 18

Responds fast! avg. 1 hour 30 minutes

2 of 3 match: Smoking allowed, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$852

Quaint Seaside Retreat With Full Gym

Hampton Bays house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

2 of 3 match: Smoking allowed, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$1,377

Hamptons Lofty Beach Barn - Pet Friendly

Water Mill house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

Responds fast! avg. 1 hour 38 minutes

2 of 3 match: Smoking allowed, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$1,718

Steve's Place: Heated Pool, 3BR Southold Home, Beach

Southold house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 17 minutes

2 of 3 match: Smoking allowed, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$224

The Lindsay Luxurious Estate: Heated Pool, Hot tub, Huge Yard

Wading River house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

Responds fast! avg. 2 hours 17 minutes

2 of 3 match: Smoking allowed, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$459

North Fork Oasis: Heated Pool, Hot tub, Steps to the beach!

Laurel house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

Responds fast! avg. 2 hours 17 minutes

2 of 3 match: Smoking allowed, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$819

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