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** Private Berkshire Escape** Monthly Pricing Available

Lee house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$659

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$226

Cozy Moose Log Cabin - Pool, Trails, Secluded Retreat

Newtown house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$374

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Fox Hill Condo - BEST LOCATION!

Stowe condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$287

Mansion & Private 3.5 Acre Estate

Bloomfield manor house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Rental types, Private outdoor pool (unheated)

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Price per night from

$916

Reading Farms Estate/ Vermont Luxury Rental

Reading villa

  • 15 bedrooms
  • 12 bathrooms
  • sleeps 46

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$5,096

Spacious 3+ Bedroom Resort Home, Sleeps 8 at Topnotch Resort & Spa

Stowe house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$860

Clarke's Landing

Middlefield house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Rental types

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Price per night from

$573

Betty's Boat House

Middlefield house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$144

Peace Barn in the heart of the CT River Valley

Deep River house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$344

Weekly Summer Beach Rental

Old Lyme house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

1 of 2 match: Private outdoor pool (unheated), Rental types

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Price per night from

$328

Country Farmhouse with Views

Shaftsbury house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$401

Whispers of the North

West Wardsboro house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 14

1 of 2 match: Private outdoor pool (unheated), Rental types

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Price per night from

$252

1 of 2 match: Private outdoor pool (unheated), Rental types

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Price per night from

$1,167

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$710

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$729

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$710

1 of 2 match: Private outdoor pool (unheated), Rental types

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Price per night from

$168

1 of 2 match: Private outdoor pool (unheated), Rental types

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Price per night from

$710

Charming Rental 3 Miles From Mt. Mansfield

Stowe house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$516

“The Perfect Vermont Getaway” When I visit Vermont in winter, I tend to go with a mixed crowd. Part of our group are avid skiers/snowboarders, the other part (well, me) are not. This house allows you to experience the best of both worlds, with something for everyone. Situated on top of the mountain (within walking distance to the lodge and with a shuttle that can pick you up right outside the front door), it's in the absolute perfect location for those who like to lace up their boots and hit the slopes. For anyone not playing snow bunny for the day, you are smack dab in the middle of Okemo with plenty of cafes, shopping, and scenic walks just down the hillside (or a very short drive away if you wish to explore). The house itself is also a fantastic, light, open space that is comfortable no matter which straw you draw for beds (we got the twins in the upstairs loft and had one of the soundest sleeps I'd had all winter). Plus, who doesn't love a hot tub. You never feel cramped even with a full house. The living room is an amazing space to just sip coffee and read your book in the morning sunshine or in front of the fire. The owners are extremely knowledgeable, responsive, and helpful, and made sure our stay was top-notch. They have everything outlined for you in a book when you arrive and are there for you should you have any questions. I can't wait to go back next winter!

1 of 2 match: Private outdoor pool (unheated), Rental types

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Price per night from

$1,832

Killington area mountain home on 60 acres and surrounded by National Forests

Pittsfield house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

1 of 2 match: Private outdoor pool (unheated), Rental types

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Price per night from

$229

Jamaica Court Cottage

New Haven house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Home Sweet Home-away-from-home” Have had the pleasure of staying in this property several times over the last few years. If you are looking for a comfortable, cozy cottage, in a quiet neighborhood close to Long Island Sound, this is it. Perfect for a couple! Family friendly! Nicely appointed. Lanna is a terrific host, attentive but never intrusive. First rate!!!

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$205

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$1,010

Flight's End-A Country Home with Babbling Brook

Hawley house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Perfect getaway” We spent few days there. It is very quiet and private. We loved the retro look. Looking forward going there again. It was New Year's eve we were hoping for.

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$218

Escape to the Berkshires!

Becket house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 11 minutes

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$315

Church sanctuary

West Dummerston house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$298

Spectacular Water Views From Every Room ~ Directly On Lake Hortonia, Vt.

Brandon house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Rental types

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Price per night from

$247

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$430

Deluxe New Home, 2 Master Suites, Tanglewood Area

Lee house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$859

The Perfect Vermont Experience for All Seasons

Dorset house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$287

Golden Triangle in the Berkshires

Hancock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$2,863

Berkshire house w/ fireplace, A/C, WiFi & laundry

Plainfield house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

“Peaceful country home” Beautiful, welcoming home in a perfect location. Warm and inviting living room; bright, airy bedrooms.

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$234

Quiet Comfortable Cabin 5 Min. Walk to Lake

Becket house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“awesome beautiful place” I can't say enough about this. Place, perfect I guess Serene, peaceful,beautiful, quiet. Djuna the owner is Sweet and very efficient and provides every detail. The Whole are is perfect Oct a getaway, things to do places To shop,eat or just cuddle in with a fire. We will Definetly be returning as soon as we can.:)))

1 of 2 match: Private outdoor pool (unheated), Rental types

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Price per night from

$171

Vermont Country Lake House

Ludlow house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$287

PARADISE on EARTH! - Historic 4BR Farmhouse

West Halifax house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$327

Killington Mountain Slopeside Home

Killington house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

“Ski home at Killington” We've been here for 10 days in late January. Wonderful place. Excellent home. We were two families with 4 aDT, CHD 4 with 6.9, 11 and 14 years. We left and came back home from skiing. We used the heated pool at the sport center. the hot tub ... We skate on the frozen pond. Although we are not accustomed to the cold (-13 F/ -25 C) for being Brazilians, we enjoyed a lot. Thank you!

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$974

Stowe Area #1 Luxury Inn - Private Rental

Stowe house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$1,718

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rentals in Pittsfield

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