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Search results; Over 1,000 homes in Pittsfield

Top guest favourite
Cabin in Pittsfield
Tiny Vermont Cabin!
1 bedroom, 1 bed, 1 private bathroom
25–30 Jul
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4.98 out of 5 average rating, 189 reviews
Bungalow in Pittsfield
Woodland Retreat ~ Green Mtns ~ Hike Bike Ski
2 bedrooms, 4 beds, 1 bathroom
22–27 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Pittsfield
Romantic Retreat, Hot Tub, near Killington Mtn
2 bedrooms, 2 beds, 1 bathroom
8–13 Aug
4.96 out of 5 average rating, 49 reviews
Guest favourite
Home in Pittsfield
Green Mountain/Killington Getaway
3 bedrooms, 6 beds, 2 bathrooms
21–26 Jul
4.84 out of 5 average rating, 88 reviews
Top guest favourite
Guest suite in Stockbridge
Studio Suite with Vermont Style & Amazing Views
1 bedroom, 1 bed, 1 bathroom
4–9 Aug
5.0 out of 5 average rating, 115 reviews
Guest favourite
Flat in Killington
Cozy Vermont Escape • Spa & Pool Retreat
2 beds, 1 bathroom
21–26 Jul
4.92 out of 5 average rating, 49 reviews
Guest favourite
Home in Stockbridge
Ski Home/Arcade Mountain Views Near Killington/Woo
3 bedrooms, 6 beds, 2.5 bathrooms
26–31 Jul
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Apartment in Killington
Bright Ski on/off Condo Full Kitchen-Free Shuttle!
2 beds, 1 bathroom
9–14 Aug
4.95 out of 5 average rating, 214 reviews
Flat in Rutland
Skier's dream, hiker's paradise!
1 bedroom, 8 beds, 1 bathroom
21–26 Jul
New place to stay
Top guest favourite
Flat in Killington
Jack S'Bearo- AC, Pool, Mountain Views, Hiking Gym
1 bedroom, 2 beds, 1 bathroom
27 Jul – 1 Aug
4.98 out of 5 average rating, 118 reviews
Top guest favourite
Home in Pittsfield
Skyeburst | Modern Mtn Home
3 bedrooms, 3 beds, 2.5 bathrooms
26–31 Jul
4.98 out of 5 average rating, 41 reviews
Top guest favourite
Cabin in Bethel
Phoebe’s Perch
1 bedroom, 3 beds, WC
26–31 Jul
5.0 out of 5 average rating, 16 reviews
Superhost
Apartment in Killington
Cozy Condo- Close to Mountain, Ski home trail
1 bedroom, 2 beds, 1 bathroom
26–31 Jul
4.83 out of 5 average rating, 179 reviews
Guest favourite
Flat in Killington
Bearitime Lodge Pool, Gym, Hot Tub Close to Resort
1 bedroom, 1 queen bed, 2 bathrooms
21–26 Jul
4.94 out of 5 average rating, 81 reviews
Guest favourite
Home in Pittsfield
The Merak Haus – a wooded retreat
3 bedrooms, 8 beds, 2.5 bathrooms
23–28 Jul
5.0 out of 5 average rating, 9 reviews
Guest favourite
Flat in Killington
BearNecessities- Pool, Hot Tub, Gym
1 bedroom, 3 beds, 1 bathroom
16–21 Aug
4.89 out of 5 average rating, 89 reviews
Top guest favourite
Home in Rochester
Tiny House set between ski resorts and mtn bikehub
1 bedroom, 1 bed, 1 bathroom
2–7 Aug
5.0 out of 5 average rating, 13 reviews
Guest favourite
Room in Tunbridge
Mountain view
1 bed, 1 bathroom
26–31 Jul
4.91 out of 5 average rating, 405 reviews
Guest favourite
Home in Pittsfield
A million-dollar view near Killington on 60 acres.
4 bedrooms, 6 beds, 1.5 bathrooms
6–11 May
4.83 out of 5 average rating, 119 reviews