Chester Rentals

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12 Houses

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

Chester house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$1,030

Great rentals within 20 miles that match your search

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Price per night from

$401

Beautiful Okemo chalet with Hot Tub

Ludlow chalet

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 16

Match: Games room

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Price per night from

$372

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

$458

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

$338

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

$1,442

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

Stratton Mountain house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Games room

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Price per night from

$2,230

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Price per night from

$285

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Price per night from

$1,373

The Grafton Lodge

Grafton lodge

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 20

Match: Games room

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Price per night from

$2,173

“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: Games room

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Price per night from

$1,830

Beautiful VT Getaway w/ Firepit - 5 min to Okemo

Ludlow house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

Match: Games room

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Price per night from

$343

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