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Stay At Jimmy's

Woodstock b&b

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$228

Great rentals within 20 miles that match your search

Killington- 6 Bedroom, 3 Bath. Right in the heart of Ski country!

Killington house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$1,088

Pico Resort Slopeside Condo, Killington Vermont

Killington condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$516

Vermont Cottage Lake Amherst

Plymouth cottage

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$802

LUXURY, hot tub, private, 6 BR, 3 BA

Killington house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

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Price per night from

$1,260

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Price per night from

$488

Suites at Killington: Luxury 2 BR Resort Ski Condo

Killington condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$166

“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

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

$373

Killington - FALL IN THE MOUNTAINS...YOU CAN'T BEAT THE VIEWS!

Killington condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$258

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

Reading Farms Estate/ Vermont Luxury Rental

Reading villa

  • 15 bedrooms
  • 12 bathrooms
  • sleeps 46

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Price per night from

$5,096

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

$103

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!

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Price per night from

$974

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

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Price per night from

$1,374

Ski Killington Vermont

Killington apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

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Price per night from

$218

Vermont Log Home On 21 Acres Btwn Okemo/killington

Mount Holly house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 14

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Price per night from

$430

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

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

$103

South Face Village

Ludlow condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$630

Oma"s Kottage

Ludlow house

  • 6 bedrooms
  • 2 bathrooms
  • sleeps 11

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Price per night from

$344

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

NEW! Luxe Lodge with Best Views, near Silver Lake+Woodstock

Barnard house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$395

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Price per night from

$189

Suites at killington Center

Killington condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$344

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Price per night from

$401

Cozy Historic Hilltop Cottage

Brownsville house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$212

Killington Vermont - 4 Bedroom, 2 Bath. Right in the heart of ski country!

Killington house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$859

Lakefront vacation home - 4 BR - sleeps 10

Ludlow house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$401

Private, peaceful home

South Pomfret house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$802

Clean/Comfortable 1 Bdrm Cabin w/NO Hidden Fees*

Killington house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$194

Killington/Rutlan 2 Bedroom w/NO Hidden Fees

Mendon house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$217

Clean/Comfortable 2 Bdroom Cabin w/No Hidden Fees*

Mendon house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$205

1820 House

Perkinsville house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$344

Farmhouse Rustic Lux on 10 acres w/ swimming pond

Bridgewater house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 22

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Price per night from

$745

☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/Sauna, Fireplace

Killington townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 8 minutes

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Price per night from

$92

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