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Search results; Over 1,000 homes in Chester

Descriptions are based on details hosts provide
Top guest favourite
Cabin in Chester
Luxe Rustic Cabin Near Okemo
4.97 out of 5 average rating, 75 reviews, 1 bedroom, 1 bed, 1 bathroom
31 Aug – 5 Sept
Top guest favourite
Home in Chester
Modern 3BR/3BA Main+River Retreat | Ski Okemo
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 6 beds, 3 bathrooms
15–20 Jul
Top guest favourite
Cabin in Chester
Cedar tiny home with sauna and pond
4.99 out of 5 average rating, 81 reviews, 1 bedroom, 1 bed, 1 bathroom
20–25 Jul
Top guest favourite
Flat in Chester
Lovely 2 Bedroom Apartment w/deck & pond view
4.93 out of 5 average rating, 164 reviews, 2 bedrooms, 3 beds, 1 bathroom
15–20 Jul
Guest favourite
Hotel in Chester
1780 inn with backyard trail access
4.86 out of 5 average rating, 77 reviews, 1 bedroom, 2 beds, 1 bathroom
16–21 Aug
Home in Chester
Private Chester Home w/ Deck, Mins to Skiing!
4.85 out of 5 average rating, 46 reviews, 3 bedrooms, 5 beds, 3 bathrooms
16–21 Jul
Top guest favourite
Home in Grafton
Restored schoolhouse with VAST trail access
4.95 out of 5 average rating, 19 reviews, 2 bedrooms, 2 beds, 2 bathrooms
23–28 Jul
Top guest favourite
Home in Baltimore
Tarbell Farm on the hill top
5.0 out of 5 average rating, 23 reviews, 2 bedrooms, 2 beds, 1 bathroom
19–24 Jul
Top guest favourite
Flat in Londonderry
Bread and Butter Apartment
4.99 out of 5 average rating, 92 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Flat in Andover
Private Hilltop farm apartment
4.97 out of 5 average rating, 472 reviews, 1 bedroom, 1 bed, 1 bathroom
20–25 Jul
Top guest favourite
Guest suite in Chester
Stone Village Private Studio
4.97 out of 5 average rating, 38 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Jul
Top guest favourite
Room in Rockingham
Visit your Craftsman home away from home-Rm 2 of 2
4.99 out of 5 average rating, 103 reviews, 1 double bed, 1 bathroom
16–21 Jul
Top guest favourite
Flat in Weathersfield
360-degree views near 3 ski mountains
4.97 out of 5 average rating, 153 reviews, 1 bedroom, 1 bed, 1 bathroom
18–23 Jul
Top guest favourite
Cabin in Grafton
Hillside log cabin with mountain views
4.94 out of 5 average rating, 17 reviews, 1 bedroom, 2 beds, 1 bathroom
30 Jul – 4 Aug
Top guest favourite
Loft in Ludlow
Renovated barn loft on 100 acres
4.95 out of 5 average rating, 895 reviews, 2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
Top guest favourite
Home in Chester
1840 stone house in historic Stone Village
5.0 out of 5 average rating, 32 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
20–25 Jul
Cabin in Newfane
Whimsical Mountain Log Cabin Retreat Near Mt Snow
New place to stay, 2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
Top guest favourite
Home in Springfield
1794 Vermont Home
5.0 out of 5 average rating, 80 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
8–13 Aug