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Villas in Chester

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The best villas in Chester

Check out our pick of great villas in Chester
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Bear Hill Views, hotel in Chester

Situated in Ludlow, Bear Hill Views is 5 km from Jackson Gore Ski Area. Okemo Mountain is 6 km away. All units include a kitchen equipped with an oven and microwave.

It's less than 10 mins drive to Okemo. It has a spacious deck and a great view of Okemo South End. This cozy cottage has 4 bedrooms, which is good for a bigger group.
Scored 8.7
8.7
Rated fabulous
Fabulous
9 reviews
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Birch House: Cozy Cabin 5 min from Okemo, hotel in Chester

Situated in Ludlow and only 40 km from Stratton Mountain, Birch House: Cozy Cabin 5 min from Okemo features accommodation with quiet street views, free WiFi and free private parking.

Scored 8.6
8.6
Rated fabulous
Fabulous
7 reviews
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Okemo Mountain Lodge, hotel in Chester

Offering mountain views, Okemo Mountain Lodge is an accommodation set in Ludlow, 41 km from Killington Mountain and 44 km from Stratton Mountain.

The location was nice and quiet. Town wasn't too far away. Everything was super cozy.
Scored 8.4
8.4
Rated very good
Very good
20 reviews
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Ludlow Escape, hotel in Chester

Ludlow Escape is situated in Ludlow, 37 km from Gifford Woods State Park, 38 km from Pico Peak, and 43 km from Mount Tom. The air-conditioned accommodation is 43 km from Stratton Mountain.

Scored 7.8
7.8
Rated good
Good
32 reviews
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Brookhaven Condos, hotel in Chester

Offering pool views, Brookhaven Condos is an accommodation located in Ludlow, 44 km from Stratton Mountain and 39 km from Gifford Woods State Park.

Scored 7.7
7.7
Rated good
Good
14 reviews
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Vermont Farm, hotel in Chester

Offering river views, Vermont Farm is an accommodation set in Proctorsville, 48 km from Stratton Mountain and 43 km from Gifford Woods State Park.

the river nearby
Scored 6.0
6.0
Rated pleasant
Pleasant
7 reviews
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Ludlow's Gem, hotel in Chester

Set in Ludlow, Ludlow's Gem is 3.4 km from Okemo Mountain. Jackson Gore Ski Area is 3.9 km away. The accommodation has a satellite TV. There is also a kitchen, fitted with a dishwasher.

Scored 9.1
9.1
Rated superb
Superb
16 reviews
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All villas in Chester
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Enjoy breakfast in Chester!

  • House At Dream Barn Hollow

    House At Dream Barn Hollow, a property with a garden, is situated in Chester, 41 km from Mount Equinox, 25 km from Dorsey Park, as well as 27 km from Bellows Falls Amtrak Station.

  • Town & Mountain
    Breakfast options

    Located in Chester, 40 km from Stratton Mountain and 46 km from Mount Equinox, Town & Mountain provides air-conditioned accommodation with a patio and free WiFi.

  • Country Riverside Retreat

    Offering a garden and river view, Country Riverside Retreat is set in Chester, 48 km from Mount Equinox and 22 km from Bellows Falls Amtrak Station.

  • Peaceful Brookside Getaway about 10 Mi to Okemo Slopes!

    Peaceful Brookside Getaway about 10 Mi to Okemo Slopes! is set in Chester, 16 km from Dorsey Park, 32 km from Bellows Falls Amtrak Station, as well as 34 km from Mount Ascutney.

  • The Brown House
    Breakfast options

    The Brown House is located in Chester, 45 km from Mount Equinox, 22 km from Bellows Falls Amtrak Station, and 35 km from Dorsey Park.

  • Zen of the Woods Tiny Cabin in Okemo Valley
    Scored 7.0
    7.0
    Rated good
    Good     · 1 review

    Situated in Chester, 48 km from Stratton Mountain and 47 km from Mount Tom, Zen of the Woods Tiny Cabin in Okemo Valley offers a garden and air conditioning.

  • Chester Charmer
    Breakfast options

    Located in Chester, 48 km from Mount Equinox and 20 km from Dorsey Park, Chester Charmer offers air conditioning.

  • Private Chester Home with Deck, Mins to Skiing!

    Private Chester Home with Deck, Mins to Skiing! is located in Chester, 45 km from Mount Tom, 15 km from Dorsey Park, and 30 km from Bellows Falls Amtrak Station.

Villas that guests love in Chester

  • Fullerton Inn & Restaurant

    Fullerton Inn & Restaurant

    Villa in Chester
    Avg. price/night: £99.30
    Scored 7.3
    7.3
    Rated good
    Good     · 241 reviews
    Positives were that it was right in the center of town so very walkable to a better breakfast and all that the cute village of Chester has to offer. The bed was firm and comfortable. The air conditioner was noisy but kept the room nice and cool. The lobby of the hotel was beautiful with a large stone fireplace and there was a veranda that was welcoming and faced the town center.
    Robin Orford
    Young couple
  • Chester Inn

    Chester Inn

    Villa in Chester
    Avg. price/night: £113.27
    Scored 8.1
    8.1
    Rated very good
    Very good     · 78 reviews
    Chester is a charming, small New England town, and Chester Inn faces the village green. The Inn has a welcoming, colonial ambience, but with modern amenities. The room was clean and comfortable, and the common rooms had a nice, homey feel.
    D
    David
    Solo traveller
  • Fullerton Inn & Restaurant

    Fullerton Inn & Restaurant

    Villa in Chester
    Avg. price/night: £99.30
    Scored 7.3
    7.3
    Rated good
    Good     · 241 reviews
    The continental breakfast included some fresh pastries. The attached restaurant was also a good value, and the three berry pie was delicious! Loved the old style historic inn, and the small village center! Hopefully, it can thrive.
    gregory
    Family with young children

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