Vacation Rentals & House Rentals in Chester

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Skiing – property near ski resort
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24 Houses

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

Chester house

5 bedrooms
4 bathrooms

sleeps 12

Match: Mountain Views

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Price per night from

$1,031

Great rentals within 20 miles that match your search

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

Bondville condo

4 bedrooms
3 bathrooms

sleeps 15

Match: Mountain Views

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Price per night from

$171

4BR / 3BA Smart Home w/ Hot Tub, Mountain View Ski Chalet 3 minutes to Stratton

Bondville house

4 bedrooms
3 bathrooms

sleeps 15

Match: Mountain Views

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Price per night from

$286

Beautiful Country Luxury Waterfront Lake Home

Unity cottage

3 bedrooms
2 bathrooms

sleeps 13

Match: Mountain Views

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Price per night from

$981

The "Okemo House" at Clocktower - WALK TO SKI TRAIL! Private Home w/ Hot Tub

Ludlow house

4 bedrooms
2 bathrooms

sleeps 12

“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: Mountain Views

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Price per night from

$1,832