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Hugging Bear Inn RENT ENTIRE INN

Chester b&b

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 18

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Price per night from

$1,234

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

Chester house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$1,031

Great rentals within 20 miles that match your search

Beautiful Country Luxury Waterfront Lake Home

Unity cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 13

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Price per night from

$982

2 Bedroom/2 Bath Condo

Stratton Mountain apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$343

Whispers of the North

West Wardsboro house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 14

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Price per night from

$253

6 BR Ski Chalet with Boats in VT Green Mountains

Ludlow chalet

  • 6 bedrooms
  • 2 bathrooms
  • sleeps 12

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Price per night from

$374

Vermont Country Lake House

Ludlow house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$287

3 Season Cabin - sleeping porch lake trails

Mount Holly log cabin

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

Responds fast! avg. 1 hour 58 minutes

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Price per night from

$104

Beautiful Okemo chalet with Hot Tub

Ludlow chalet

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 16

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Price per night from

$373

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Price per night from

$402

Lakefront vacation home - 4 BR - sleeps 10

Ludlow house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$402

Perfect Hideaway Cabin - lake, trails, forest, meadows

Mount Holly log cabin

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 58 minutes

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Price per night from

$104

South Face Village

Ludlow condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$631

Oma"s Kottage

Ludlow house

  • 6 bedrooms
  • 2 bathrooms
  • sleeps 11

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Price per night from

$345

Village Farmhouse - mins to GMHA, Okemo, Killington. Pet-friendly.

Reading house

  • 4 bedrooms
  • 1 bathroom
  • sleeps 8

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Price per night from

$287

Spectacular 50 miles Year Round Mountain View - 3+ BR Townhouse

Peru townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 2 minutes

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Price per night from

$339

Cozy Historic Hilltop Cottage

Brownsville house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$213

Fox Run -- Sleeps 10 - 12, Only 1 mile from Okemo Jackson Gore Base

Ludlow townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$459

A Family Place

Bondville house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$413

Vermont 1828 Reunion House, sleeps 16 5 miles to Okemo

Proctorsville house

  • 8 bedrooms
  • 4 bathrooms
  • sleeps 16

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Price per night from

$459

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Price per night from

$1,125

Cute VT Bungalow With 180 Degree View of NH

Springfield apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$230

Contemporary Ski Chalet Minutes to Hiking Dining Parks

South Londonderry house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$1,447

Chase House Inn - Edwin Stanton Room

Cornish house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$172

1820 House

Perkinsville house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$345

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

Stratton Mountain house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$2,237

A Quiet Retreat in Rural New Hampshire

Cornish house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$362

Modern Ski In / Ski Out 4BR / 3BA Smart Home w/ shared pool and hot tub

Bondville condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 15

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Price per night from

$171

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Price per night from

$286

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Price per night from

$1,374

Vermont Cottage on Lake Amherst 6 Bedrooms 4 Bathrooms

Plymouth cottage

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$802

Vermont Cottage Lake Amherst

Plymouth cottage

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$802

“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!

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Price per night from

$1,832

25 Acre Mtn Playground, 2 Bd, Great Ski Access, Close to Okemo, VAST trails

Ludlow apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$401

Beautiful VT Getaway w/ Firepit - 5 min to Okemo

Ludlow house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

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Price per night from

$344

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Price per night from

$401

The Grafton Lodge

Grafton lodge

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 20

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Price per night from

$2,176

Walk to ski trials on Okemo! Private Luxury Chalet

Ludlow chalet

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

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Price per night from

$1,369

Viewing 38 of 43
rentals in Chester

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