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Search results; Over 1,000 homes in Pittsfield

Descriptions are based on details hosts provide
Superhost
Hotel in Pittsfield
Clear River Inn - 2 Double Beds (Ground Floor)
1 bedroom, 2 beds, 1 private bathroom
15–20 Jul
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4.75 out of 5 average rating, 115 reviews
Bungalow in Pittsfield
Woodland Retreat ~ Green Mtns ~ Hike Bike Ski
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 4 beds, 1 bathroom
29 Jul – 3 Aug
Top guest favourite
Cabin in Pittsfield
Tiny Vermont Cabin!
4.98 out of 5 average rating, 188 reviews, 1 bedroom, 1 bed, 1 bathroom
15–20 Jul
Top guest favourite
Home in Pittsfield
Killington area entire Inn to yourself! 14bd/15bth
5.0 out of 5 average rating, 18 reviews, 14 bedrooms, 24 beds, 15 bathrooms
19–24 Jul
Guest favourite
Home in Pittsfield
Romantic Retreat, Hot Tub, near Killington Mtn
4.96 out of 5 average rating, 48 reviews, 2 bedrooms, 2 beds, 1 bathroom
25–30 Jul
Top guest favourite
Home in Pittsfield
Killington area Inn all to yourself! 9bd/10 bath
5.0 out of 5 average rating, 52 reviews, 9 bedrooms, 14 beds, 10 bathrooms
23–28 Jul
Top guest favourite
Home in Stockbridge
Arcade room with mountain views near Killington
5.0 out of 5 average rating, 21 reviews, 3 bedrooms, 6 beds, 2.5 bathrooms
26–31 Jul
Guest favourite
Home in Pittsfield
Peak Hill – 3 Bedroom, Hot Tub. Car Charger!
5.0 out of 5 average rating, 20 reviews, 3 bedrooms, 5 beds, 2 bathrooms
15–20 Jul
Top guest favourite
Home in Pittsfield
Skyeburst | Modern Mtn Home
4.98 out of 5 average rating, 40 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
19–24 Jul
Top guest favourite
Flat in Killington
BearNecessities- Pool, Hot Tub, Gym
4.89 out of 5 average rating, 88 reviews, 1 bedroom, 3 beds, 1 bathroom
5–10 Aug
Guest favourite
Home in Pittsfield
The Merak Haus – a wooded retreat
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 8 beds, 2.5 bathrooms
17–22 Jul
Top guest favourite
Flat in Killington
Ski-in/ski-out with a wood-burning fireplace
4.98 out of 5 average rating, 117 reviews, 1 bedroom, 2 beds, 1 bathroom
19–24 Jul
Top guest favourite
Holiday home in Pittsfield
Hot tub and fire pit near Killington
4.9 out of 5 average rating, 63 reviews, 4 bedrooms, 7 beds, 4.5 bathrooms
15–20 Jul
Top guest favourite
Home in Stockbridge
Unique Mountain Retreat
5.0 out of 5 average rating, 42 reviews, 4 bedrooms, 7 beds, 2 bathrooms
15–20 Jul
Guest favourite
Home in Pittsfield
Wood stove and deck overlooking mountain woods
4.84 out of 5 average rating, 88 reviews, 3 bedrooms, 6 beds, 2 bathrooms
15–20 Jul
Guest favourite
Hotel in Pittsfield
Clear River Inn - 1 King Bed (Ground Floor)
4.76 out of 5 average rating, 25 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Jul
Guest favourite
Home in Pittsfield
VT Cabin, close to Killington Mountain and lakes.
4.96 out of 5 average rating, 47 reviews, 5 bedrooms, 4 beds, 3 bathrooms
15–20 Jul
Top guest favourite
Guest suite in Stockbridge
Mountain views with a fire pit
5.0 out of 5 average rating, 115 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Aug
Guest favourite
Home in Pittsfield
Deck overlooking the brook, wood stove
5.0 out of 5 average rating, 14 reviews, 3 bedrooms, 5 beds, 2 bathrooms
15–20 Jul