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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
9–14 Aug
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4.98 out of 5 average rating, 190 reviews
Top guest favourite
Flat in Killington
Jack S'Bearo- AC, Pool, Mountain Views, Hiking Gym
1 bedroom, 2 beds, 1 bathroom
2–7 Aug
4.98 out of 5 average rating, 119 reviews
Guest favourite
Home in Pittsfield
Romantic Retreat, Hot Tub, near Killington Mtn
2 bedrooms, 2 beds, 1 bathroom
8–13 Aug
4.94 out of 5 average rating, 50 reviews
Top guest favourite
Home in Pittsfield
Skyeburst | Modern Mtn Home
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Aug
4.98 out of 5 average rating, 42 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
Peak Hill – 3 Bedroom, Hot Tub. Car Charger!
3 bedrooms, 5 beds, 2 bathrooms
1–6 Aug
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Chalet in Stockbridge
Cozy Vermont Chalet
4 bedrooms, 9 beds, 2 bathrooms
3–8 Jan
4.94 out of 5 average rating, 103 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
Home in Stockbridge
Ski Home/Arcade Mountain Views Near Killington/Woo
3 bedrooms, 6 beds, 2.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Cabin in Bethel
Phoebe’s Perch
1 bedroom, 3 beds, WC
16–21 Aug
5.0 out of 5 average rating, 19 reviews
Guest favourite
Home in Pittsfield
Green Mountain/Killington Getaway
3 bedrooms, 6 beds, 2 bathrooms
1–6 Aug
4.84 out of 5 average rating, 88 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
Guest favourite
Hotel in Pittsfield
Clear River Inn - 1 King Bed (Ground Floor)
1 bedroom, 1 king bed, 1 bathroom
1–6 Aug
4.77 out of 5 average rating, 26 reviews
Guest favourite
Home in Stockbridge
Little House on the Green
1 bedroom, 4 beds, 1 bathroom
2–7 Apr
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Killington
Snowarts- Game room, Fireplace, Close to golf!
3 bedrooms, 7 beds, 2 bathrooms
1–6 Aug
4.97 out of 5 average rating, 79 reviews
Superhost
Apartment in Killington
Fall Line G2A: Small Studio For 2. Hot Tub|Shuttle
1 bedroom, 2 single beds, 1 bathroom
2–7 Aug
4.67 out of 5 average rating, 36 reviews
Guest favourite
Home in Pittsfield
Riverside Retreat: Hike & Bike From Your Doorstep
3 bedrooms, 6 beds, 2.5 bathrooms
9–14 Aug
4.95 out of 5 average rating, 63 reviews
Guest favourite
Home in Pittsfield
Killington area home - 4 seasons - hot tub and A/C
3 bedrooms, 10 beds, 2.5 bathrooms
16–21 Aug
4.85 out of 5 average rating, 256 reviews
Top guest favourite
Home in Killington
CozyDen - AC, Grill, Bike to Mountain, Porch!
1 bedroom, 2 beds, 1 bathroom
16–21 Aug
4.98 out of 5 average rating, 206 reviews