Vacation Rentals & Cabins in Vermont

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Mansion & Private 3.5 Acre Estate

Bloomfield manor house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Ceiling Fans Games room Linen provided Private outdoor pool (unheated) Private pool

All filters match

Price per night from

$918

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Fox Hill Condo - BEST LOCATION!

Stowe condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

4 of 5 match: Ceiling Fans, Games room, Linen provided, Private outdoor pool (unheated), Private pool

4 of 5 filters match

Price per night from

$287

Christmas in The Berkshires

Hancock condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

3 of 5 match: Private outdoor pool (unheated), Private pool, Ceiling Fans, Games room, Linen provided

3 of 5 filters match

Price per night from

$259

3 of 5 match: Private outdoor pool (unheated), Private pool, Ceiling Fans, Games room, Linen provided

3 of 5 filters match

Price per night from

$286

Enjoy horses and the largest recreational lake in Massachusetts

East Otis apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 5 match: Private outdoor pool (unheated), Private pool, Ceiling Fans, Games room, Linen provided

3 of 5 filters match

Price per night from

$126

Beautiful VT Getaway w/ Firepit - 5 min to Okemo

Ludlow house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

3 of 5 match: Private outdoor pool (unheated), Private pool, Ceiling Fans, Games room, Linen provided

3 of 5 filters match

Price per night from

$344

Stowe Area #1 Luxury Inn - Private Rental

Stowe house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

3 of 5 match: Private outdoor pool (unheated), Private pool, Ceiling Fans, Games room, Linen provided

3 of 5 filters match

Price per night from

$1,723

3 of 5 match: Private outdoor pool (unheated), Private pool, Ceiling Fans, Games room, Linen provided

3 of 5 filters match

Price per night from

$402

Contemporary Ski Chalet Minutes to Hiking Dining Parks

South Londonderry house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

3 of 5 match: Private outdoor pool (unheated), Private pool, Ceiling Fans, Games room, Linen provided

3 of 5 filters match

Price per night from

$1,447

INDESCRIBALE Mountain View Getaway! Tons of Amenities!

Shrewsbury house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 20

Responds fast! avg. 37 minutes

3 of 5 match: Private outdoor pool (unheated), Private pool, Ceiling Fans, Games room, Linen provided

3 of 5 filters match

Price per night from

$458

BEAUTIFUL STRATTON! 5 BEDS-5 BATHS HOME w/VIEWS, ON SHUTTLE

Stratton Mountain house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

3 of 5 match: Private outdoor pool (unheated), Private pool, Ceiling Fans, Games room, Linen provided

3 of 5 filters match

Price per night from

$2,238

“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!

3 of 5 match: Private outdoor pool (unheated), Private pool, Ceiling Fans, Games room, Linen provided

3 of 5 filters match

Price per night from

$1,832

Work, Hike, Ski, Relax - Big Restored 1860s Farmhouse

Chester house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

3 of 5 match: Private outdoor pool (unheated), Private pool, Ceiling Fans, Games room, Linen provided

3 of 5 filters match

Price per night from

$1,031

3 of 5 match: Private outdoor pool (unheated), Private pool, Ceiling Fans, Games room, Linen provided

3 of 5 filters match

Price per night from

$1,374

The Grafton Lodge

Grafton lodge

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 20

3 of 5 match: Private outdoor pool (unheated), Private pool, Ceiling Fans, Games room, Linen provided

3 of 5 filters match

Price per night from

$2,176

Contemporary Spacious 7br/6.5 bath home near Killington VT

Mendon house

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 22

3 of 5 match: Private outdoor pool (unheated), Private pool, Ceiling Fans, Games room, Linen provided

3 of 5 filters match

Price per night from

$916

3 of 5 match: Private outdoor pool (unheated), Private pool, Ceiling Fans, Games room, Linen provided

3 of 5 filters match

Price per night from

$489

Spectacular Log Cabin w/ Mountain Views near Lake

Ferrisburgh log cabin

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

3 of 5 match: Private outdoor pool (unheated), Private pool, Ceiling Fans, Games room, Linen provided

3 of 5 filters match

Price per night from

$458

3 of 5 match: Private outdoor pool (unheated), Private pool, Ceiling Fans, Games room, Linen provided

3 of 5 filters match

Price per night from

$459

3 of 5 match: Private outdoor pool (unheated), Private pool, Ceiling Fans, Games room, Linen provided

3 of 5 filters match

Price per night from

$572

Smugglers' Notch * 2 Bedroom, Sleeps 8

Cambridge condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 5 match: Private outdoor pool (unheated), Private pool, Ceiling Fans, Games room, Linen provided

3 of 5 filters match

Price per night from

$452

Cozy Moose Log Cabin - Pool, Trails, Secluded Retreat

Newtown house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

3 of 5 match: Ceiling Fans, Games room, Linen provided, Private outdoor pool (unheated), Private pool

3 of 5 filters match

Price per night from

$331

** Private Berkshire Escape** Monthly Pricing Available

Lee house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

3 of 5 match: Ceiling Fans, Games room, Linen provided, Private outdoor pool (unheated), Private pool

3 of 5 filters match

Price per night from

$659

Reading Farms Estate/ Vermont Luxury Rental

Reading villa

  • 15 bedrooms
  • 12 bathrooms
  • sleeps 46

3 of 5 match: Ceiling Fans, Games room, Linen provided, Private outdoor pool (unheated), Private pool

3 of 5 filters match

Price per night from

$5,106

Large Family Home Near Five Colleges

Hadley house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

2 of 5 match: Ceiling Fans, Private outdoor pool (unheated), Private pool, Games room, Linen provided

2 of 5 filters match

Price per night from

$2,007

River House in the Heart of Middlebury

Middlebury house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Responds fast! avg. 3 hours 15 minutes

2 of 5 match: Ceiling Fans, Private outdoor pool (unheated), Private pool, Games room, Linen provided

2 of 5 filters match

Price per night from

$245

Quintessential Vermont Farmhouse

Waitsfield house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

2 of 5 match: Ceiling Fans, Private outdoor pool (unheated), Private pool, Games room, Linen provided

2 of 5 filters match

Price per night from

$373

Beautiful Okemo chalet with Hot Tub

Ludlow chalet

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 16

2 of 5 match: Linen provided, Private outdoor pool (unheated), Private pool, Ceiling Fans, Games room

2 of 5 filters match

Price per night from

$373

2 of 5 match: Ceiling Fans, Games room, Linen provided, Private outdoor pool (unheated), Private pool

2 of 5 filters match

Price per night from

$218

Stowe Chalet, Mountain Views, Warm, Cozy, Quiet and Private

Morrisville chalet

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 5 match: Ceiling Fans, Private outdoor pool (unheated), Private pool, Games room, Linen provided

2 of 5 filters match

Price per night from

$228

The Equinox Golf Resort & Spa

Manchester house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 5 match: Ceiling Fans, Private outdoor pool (unheated), Private pool, Games room, Linen provided

2 of 5 filters match

Price per night from

$772

The Equinox Golf Resort & Spa

Manchester house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

2 of 5 match: Ceiling Fans, Private outdoor pool (unheated), Private pool, Games room, Linen provided

2 of 5 filters match

Price per night from

$970

Back Inn Time--The Loft

Saint Albans apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 5 match: Games room, Private outdoor pool (unheated), Private pool, Ceiling Fans, Linen provided

2 of 5 filters match

Price per night from

$362

Vermont 1828 Reunion House, sleeps 16 5 miles to Okemo

Proctorsville house

  • 8 bedrooms
  • 4 bathrooms
  • sleeps 16

2 of 5 match: Ceiling Fans, Private outdoor pool (unheated), Private pool, Games room, Linen provided

2 of 5 filters match

Price per night from

$459

Sunlit Apartment w/ Parking & Gym Downtown at Yale

New Haven apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 5 match: Ceiling Fans, Private outdoor pool (unheated), Private pool, Games room, Linen provided

2 of 5 filters match

Price per night from

$521

Luxurious 2BR - 2Bath W/ Gym | Downtown at Yale

New Haven apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 5 match: Ceiling Fans, Private outdoor pool (unheated), Private pool, Games room, Linen provided

2 of 5 filters match

Price per night from

$1,182

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

South Lee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 5 match: Ceiling Fans, Private outdoor pool (unheated), Private pool, Games room, Linen provided

2 of 5 filters match

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

2 of 5 match: Ceiling Fans, Private outdoor pool (unheated), Private pool, Games room, Linen provided

2 of 5 filters match

Price per night from

$81

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