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Search results; Over 1,000 homes in Pittsfield

Guest favourite
Hotel in Pittsfield
Clear River Inn - 2 Double Beds (2nd Floor)
1 bedroom, 2 beds, 1 private bathroom
1–6 Aug
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4.88 out of 5 average rating, 129 reviews
Bungalow in Pittsfield
Woodland Retreat ~ Green Mtns ~ Hike Bike Ski
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 4 beds, 1 bathroom
22–27 Aug
Top guest favourite
Cabin in Pittsfield
Tiny Vermont Cabin!
4.98 out of 5 average rating, 190 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Guest favourite
Home in Pittsfield
Romantic Retreat, Hot Tub, near Killington Mtn
4.94 out of 5 average rating, 50 reviews, 2 bedrooms, 2 beds, 1 bathroom
8–13 Aug
Top guest favourite
Home in Pittsfield
Skyeburst | Modern Mtn Home
4.98 out of 5 average rating, 42 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Aug
Guest favourite
Home in Stockbridge
Ski Home/Arcade Mountain Views Near Killington/Woo
5.0 out of 5 average rating, 22 reviews, 3 bedrooms, 6 beds, 2.5 bathrooms
16–21 Aug
Guest favourite
Home in Pittsfield
Peak Hill – 3 Bedroom, Hot Tub. Car Charger!
5.0 out of 5 average rating, 21 reviews, 3 bedrooms, 5 beds, 2 bathrooms
6–11 Aug
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
1–6 Aug
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
1–6 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
1–6 Aug
Guest favourite
Home in Pittsfield
Killington area home - 4 seasons - hot tub and A/C
4.85 out of 5 average rating, 256 reviews, 3 bedrooms, 10 beds, 2.5 bathrooms
16–21 Aug
Top guest favourite
Home in Pittsfield
Killington area entire Inn to yourself! 14bd/15bth
5.0 out of 5 average rating, 19 reviews, 14 bedrooms, 24 beds, 15 bathrooms
6–11 Aug
Top guest favourite
Home in Stockbridge
Unique Mountain Retreat
5.0 out of 5 average rating, 42 reviews, 4 bedrooms, 7 beds, 2 bathrooms
1–6 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
23–28 Aug
Guest favourite
Home in Killington
Entire home- Killington, Vermont Ski, Hike, Bike
5.0 out of 5 average rating, 18 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
2–7 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
1–6 Aug
Guest favourite
Chalet in Stockbridge
Vermont Chalet
4.85 out of 5 average rating, 199 reviews, 2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
Guest favourite
Home in Killington
Killington Chalet: Hot Tub, Fireplace, spacious 4b
4.94 out of 5 average rating, 67 reviews, 4 bedrooms, 5 beds, 2 bathrooms
30 Aug – 4 Sept
Top guest favourite
Chalet in Stockbridge
Gnome Home Mountain Ski Chalet w/Sauna Killington
4.97 out of 5 average rating, 163 reviews, 4 bedrooms, 6 beds, 2 bathrooms
2–7 Aug