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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
2 bedrooms, 4 beds
22–27 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Cabin in Pittsfield
Tiny Vermont Cabin!
1 bedroom, 1 queen bed
8–13 Aug
4.98 out of 5 average rating, 189 reviews
Top guest favourite
Home in Pittsfield
Skyeburst | Modern Mtn Home
3 bedrooms, 3 beds
1–6 Aug
4.98 out of 5 average rating, 41 reviews
Guest favourite
Home in Pittsfield
Peak Hill – 3 Bedroom, Hot Tub. Car Charger!
3 bedrooms, 5 beds
1–6 Aug
5.0 out of 5 average rating, 21 reviews
Guest favourite
Home in Pittsfield
Romantic Retreat, Hot Tub, near Killington Mtn
2 bedrooms, 2 beds
8–13 Aug
4.96 out of 5 average rating, 49 reviews
Top guest favourite
Home in Killington
CozyDen - AC, Grill, Bike to Mountain, Porch!
1 bedroom, 2 beds
16–21 Aug
4.98 out of 5 average rating, 205 reviews
Top guest favourite
Home in Stockbridge
Riverfront Retreat in Stockbridge
3 bedrooms, 4 beds
2–7 Aug
5.0 out of 5 average rating, 31 reviews
Guest favourite
Home in Pittsfield
Green Mountain/Killington Getaway
3 bedrooms, 6 beds
1–6 Aug
4.84 out of 5 average rating, 88 reviews
Top guest favourite
Flat in Killington
Jack S'Bearo- AC, Pool, Mountain Views, Hiking Gym
1 bedroom, 2 beds
1–6 Aug
4.98 out of 5 average rating, 118 reviews
Top guest favourite
Guest suite in Stockbridge
Studio Suite with Vermont Style & Amazing Views
1 bedroom, 1 bed
4–9 Aug
5.0 out of 5 average rating, 115 reviews
Top guest favourite
Apartment in Killington
Bright Ski on/off Condo Full Kitchen-Free Shuttle!
2 beds
9–14 Aug
4.95 out of 5 average rating, 214 reviews
Guest favourite
Home in Stockbridge
Ski Home/Arcade Mountain Views Near Killington/Woo
3 bedrooms, 6 beds
16–21 Aug
5.0 out of 5 average rating, 22 reviews
Guest favourite
Home in Killington
Entire home- Killington, Vermont Ski, Hike, Bike
3 bedrooms, 4 beds
2–7 Aug
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Stockbridge
Little House on the Green
1 bedroom, 4 beds
2–7 Apr
5.0 out of 5 average rating, 13 reviews
Guest favourite
Cabin in Goshen
The Berghüttli: Glowing Swiss Hut in the Forest
2 bedrooms, 2 beds
29 Aug – 3 Sept
4.97 out of 5 average rating, 143 reviews
Top guest favourite
Room in Mendon
Private fireplace suite & luxury bath - Killington
1 queen bed
10–15 Aug
4.99 out of 5 average rating, 829 reviews
Guest favourite
Home in Pittsfield
Killington area home - 4 seasons - hot tub and A/C
3 bedrooms, 10 beds
16–21 Aug
4.85 out of 5 average rating, 256 reviews
Top guest favourite
Home in Pittsfield
The Fiddlehead Lodge (Green Mountain Getaway)
4 bedrooms, 9 beds
2–7 Aug
5.0 out of 5 average rating, 13 reviews