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Hugging Bear Inn RENT ENTIRE INN

Chester b&b

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 18

Match: Children under 5

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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

Match: Children under 5

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Price per night from

$1,031

Great rentals within 20 miles that match your search

2 Bedroom/2 Bath Condo

Stratton Mountain apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Children under 5

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Price per night from

$344

Whispers of the North

West Wardsboro house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 14

Match: Children under 5

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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

Match: Children under 5

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Price per night from

$373

Vermont Country Lake House

Ludlow house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Children under 5

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Price per night from

$287

Match: Children under 5

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Price per night from

$402

Vermont Log Home On 21 Acres Btwn Okemo/killington

Mount Holly house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 14

Match: Children under 5

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Price per night from

$431

Cozy Historic Hilltop Cottage

Brownsville house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Children under 5

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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

Match: Children under 5

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Price per night from

$459

Perfect Hideaway Cabin - lake, trails, forest, meadows

Mount Holly log cabin

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 58 minutes

Match: Children under 5

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Price per night from

$104

South Face Village

Ludlow condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Children under 5

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Price per night from

$632

Oma"s Kottage

Ludlow house

  • 6 bedrooms
  • 2 bathrooms
  • sleeps 11

Match: Children under 5

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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

Match: Children under 5

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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

Match: Children under 5

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Price per night from

$339

Lakefront vacation home - 4 BR - sleeps 10

Ludlow house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Children under 5

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Price per night from

$402

A Family Place

Bondville house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Children under 5

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Price per night from

$414

Vermont 1828 Reunion House, sleeps 16 5 miles to Okemo

Proctorsville house

  • 8 bedrooms
  • 4 bathrooms
  • sleeps 16

Match: Children under 5

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Price per night from

$459

Match: Children under 5

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Price per night from

$1,125

1820 House

Perkinsville house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Children under 5

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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

Match: Children under 5

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Price per night from

$2,238

A Quiet Retreat in Rural New Hampshire

Cornish house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Children under 5

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Price per night from

$362

3 Season Cabin - sleeping porch lake trails

Mount Holly log cabin

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

Responds fast! avg. 1 hour 58 minutes

Match: Children under 5

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Price per night from

$104

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

Bondville condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 15

Match: Children under 5

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Price per night from

$171

Beautiful Country Luxury Waterfront Lake Home

Unity cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 13

Match: Children under 5

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Price per night from

$981

Beautiful Okemo chalet with Hot Tub

Ludlow chalet

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 16

Match: Children under 5

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Price per night from

$373

Match: Children under 5

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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

Match: Children under 5

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Price per night from

$802

Vermont Cottage Lake Amherst

Plymouth cottage

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Children under 5

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Price per night from

$802

Contemporary Ski Chalet Minutes to Hiking Dining Parks

South Londonderry house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Children under 5

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Price per night from

$1,444

Match: Children under 5

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Price per night from

$286

Okemo Mountain Lodge A-108 Ski In/Ski Out

Ludlow condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Children under 5

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Price per night from

$229

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

Ludlow apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Children under 5

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Price per night from

$401

“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!

Match: Children under 5

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Price per night from

$1,832

Walk to ski trials on Okemo! Private Luxury Chalet

Ludlow chalet

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

Match: Children under 5

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Price per night from

$1,369

Multi Level Stratton Mountain Retreat

Bondville house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 16

Match: Children under 5

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Price per night from

$1,145

The Grafton Lodge

Grafton lodge

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 20

Match: Children under 5

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Price per night from

$2,176

Beautiful VT Getaway w/ Firepit - 5 min to Okemo

Ludlow house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

Match: Children under 5

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Price per night from

$344

Viewing 38 of 42
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