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Search results; Over 1,000 homes in Pittsfield

Top guest favourite
Cabin in Pittsfield
Tiny Vermont Cabin!
1 bedroom, 1 bed, 1 private bathroom
30 Aug – 4 Sept
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4.98 out of 5 average rating, 192 reviews
Guest favourite
Home in Pittsfield
Romantic Retreat, Hot Tub, near Killington Mtn
2 bedrooms, 2 beds, 1 bathroom
19–24 Aug
4.94 out of 5 average rating, 51 reviews
Bungalow in Pittsfield
Woodland Retreat ~ Green Mtns ~ Hike Bike Ski
2 bedrooms, 4 beds, 1 bathroom
21–26 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Guest suite in Stockbridge
Studio Suite with Vermont Style & Amazing Views
1 bedroom, 1 bed, 1 bathroom
8–13 Aug
5.0 out of 5 average rating, 116 reviews
Top guest favourite
Home in Pittsfield
Skyeburst | Modern Mtn Home
3 bedrooms, 3 beds, 2.5 bathrooms
16–21 Aug
4.98 out of 5 average rating, 42 reviews
Guest favourite
Home in Pittsfield
Post & Beam Vermont Farmhouse | Near Killington
3 bedrooms, 4 beds, 2.5 bathrooms
4–9 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Cabin in Brandon
Honeycrisp Cabin
1 bedroom, 1 bed, 1 bathroom
16–21 Aug
4.97 out of 5 average rating, 36 reviews
Top guest favourite
Cottage in Windsor
Ogden's Mill Farm
2 bedrooms, 3 beds, 1 bathroom
4–9 Nov
4.97 out of 5 average rating, 462 reviews
Guest favourite
Home in Pittsfield
Peak Hill – 3 Bedroom, Hot Tub. Car Charger!
3 bedrooms, 5 beds, 2 bathrooms
8–13 Aug
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Rochester
The Guest House at Sky Hollow
2 bedrooms, 2 beds, 1.5 bathrooms
25–30 Aug
4.97 out of 5 average rating, 236 reviews
Top guest favourite
Place to stay in Middletown Springs
Off-Grid Meadow Cabin Glamping Retreat
1 bedroom, 1 queen bed, WC
12–17 Aug
5.0 out of 5 average rating, 36 reviews
Top guest favourite
Flat in Hancock
1882 Farmhouse - a cozy haven close to everything
2 bedrooms, 2 beds, 1 bathroom
17–22 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Cabin in Bethel
The Gourmet Cabin at Stitchdown Farm
1 bedroom, 1 queen bed, 1 bathroom
17–22 Aug
4.95 out of 5 average rating, 108 reviews
Top guest favourite
Home in Stockbridge
Riverfront Retreat in Stockbridge
3 bedrooms, 4 beds, 1.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 34 reviews
Top guest favourite
Cabin in Bethel
Firefly Cottage
1 bedroom, 1 bed, 1 bathroom
25–30 Oct
4.97 out of 5 average rating, 96 reviews
Top guest favourite
Yurt in Pittsford
Remote Cozy Yurt with Sunset Views
1 bedroom, 3 beds, 1.5 bathrooms
10–15 Aug
4.97 out of 5 average rating, 171 reviews
Top guest favourite
Home in Rochester
Tiny House set between ski resorts and mtn bikehub
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Barnard
The Looking Glass, a modernistic escape
1 bedroom, 1 bed, 1.5 bathrooms
31 Aug – 5 Sept
4.97 out of 5 average rating, 39 reviews
Top guest favourite
Rooms in Mendon
Cozy private room - Killington
2 bedrooms, 1 queen bed, 1 bathroom
18–23 Aug
4.98 out of 5 average rating, 595 reviews