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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, 189 reviews, 1 bedroom, 1 bed, 1 bathroom
8–13 Aug
Top guest favourite
Home in Pittsfield
Skyeburst | Modern Mtn Home
4.98 out of 5 average rating, 41 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
1–6 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
1–6 Aug
Guest favourite
Home in Pittsfield
Romantic Retreat, Hot Tub, near Killington Mtn
4.96 out of 5 average rating, 49 reviews, 2 bedrooms, 2 beds, 1 bathroom
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
1–6 Aug
Top guest favourite
Cabin in Bethel
Phoebe’s Perch
5.0 out of 5 average rating, 16 reviews, 1 bedroom, 3 beds, WC
3–8 Aug
Top guest favourite
Home in Stockbridge
Riverfront Retreat in Stockbridge
5.0 out of 5 average rating, 31 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
2–7 Aug
Top guest favourite
Apartment in Killington
Bright Ski on/off Condo Full Kitchen-Free Shuttle!
4.95 out of 5 average rating, 214 reviews, 2 beds, 1 bathroom
9–14 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
Top guest favourite
Home in Killington
CozyDen - AC, Grill, Bike to Mountain, Porch!
4.98 out of 5 average rating, 203 reviews, 1 bedroom, 2 beds, 1 bathroom
16–21 Aug
Superhost
Bed and breakfast in Killington
Twin Room with Private Bath - The Trailside Inn
4.83 out of 5 average rating, 23 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Aug
Top guest favourite
Flat in Killington
Jack S'Bearo- AC, Pool, Mountain Views, Hiking Gym
4.98 out of 5 average rating, 118 reviews, 1 bedroom, 2 beds, 1 bathroom
1–6 Aug
Guest favourite
Home in Pittsfield
A million-dollar view near Killington on 60 acres.
4.83 out of 5 average rating, 119 reviews, 4 bedrooms, 6 beds, 1.5 bathrooms
6–11 May
Top guest favourite
Home in Pittsfield
The Fiddlehead Lodge (Green Mountain Getaway)
5.0 out of 5 average rating, 13 reviews, 4 bedrooms, 9 beds, 1.5 bathrooms
2–7 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
Room in Mendon
Private fireplace suite & luxury bath - Killington
4.99 out of 5 average rating, 828 reviews, 1 queen bed, 1 bathroom
10–15 Aug
Guest favourite
Room in Tunbridge
Robert Duncan Room
4.9 out of 5 average rating, 189 reviews, 1 bed, No bathroom
1–6 Aug