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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
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
Guest favourite
Home in Killington
Killington Condo Near Mountain Biking Trails
4.94 out of 5 average rating, 63 reviews, 2 bedrooms, 5 beds, 2 bathrooms
15–20 Jul
Guest favourite
Home in Pittsfield
Hot tub and slope views from deck
5.0 out of 5 average rating, 20 reviews, 3 bedrooms, 5 beds, 2 bathrooms
15–20 Jul
Guest favourite
Home in Pittsfield
Post-and-beam farmhouse on 500 private acres
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
7–12 Sept
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
Home in Stockbridge
Ski Home/Arcade Mountain Views Near Killington/Woo
5.0 out of 5 average rating, 21 reviews, 3 bedrooms, 6 beds, 2.5 bathrooms
26–31 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
Cabin in Bethel
Nordic-style cabin on 140 woodland acres
4.97 out of 5 average rating, 86 reviews, 1 bedroom, 1 bed, 1 bathroom
25–30 Oct
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
Guest favourite
Home in Killington
Killington Chalet: Hot Tub, Fireplace, spacious 4b
4.94 out of 5 average rating, 66 reviews, 4 bedrooms, 5 beds, 2 bathrooms
24–29 Aug
Top guest favourite
Home in Killington
Hot tub|Sauna|Movie Room! 8 min to Killington Mtn!
5.0 out of 5 average rating, 50 reviews, 4 bedrooms, 7 beds, 4 bathrooms
8–13 Aug
Guest favourite
Home in Pittsfield
Green Mountain/Killington Getaway
4.84 out of 5 average rating, 88 reviews, 3 bedrooms, 6 beds, 2 bathrooms
15–20 Jul
Guest favourite
Cabin in Goshen
Glowing maple hut in the forest
4.97 out of 5 average rating, 141 reviews, 2 bedrooms, 2 beds, 1 bathroom
19–24 Jul
Guest favourite
Home in Pittsfield
Two decks and a fire pit near Killington
4.96 out of 5 average rating, 47 reviews, 5 bedrooms, 4 beds, 3 bathrooms
15–20 Jul
Guest favourite
Chalet in Stockbridge
11 private acres with a pond
4.86 out of 5 average rating, 196 reviews, 2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
Top guest favourite
Cabin in Leicester
Log Cabin Getaway near Middlebury and Green Mtns
4.98 out of 5 average rating, 876 reviews, 2 bedrooms, 3 beds, 1 bathroom
11–16 Aug