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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
,
4.98 out of 5 average rating, 193 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, 5 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, 43 reviews
Guest favourite
Home in Pittsfield
Peak Hill – 3 Bedroom, Hot Tub. Car Charger!
3 bedrooms, 5 beds, 2 bathrooms
11–16 Aug
5.0 out of 5 average rating, 22 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
Home in Rochester
Iron Springs Cabin (Black Haus 2.0)
1 bedroom, 1 queen bed, 1 bathroom
26–31 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Tiny home in Pittsfield
Tiny Home: VT Mountain Cabin
1 bedroom, 2 beds, 1 bathroom
1–6 May
5.0 out of 5 average rating, 40 reviews
Top guest favourite
Guest suite in Stockbridge
Studio Suite with Vermont Style & Amazing Views
1 bedroom, 1 bed, 1 bathroom
11–16 Aug
5.0 out of 5 average rating, 116 reviews
Top guest favourite
Home in Mendon
New Firepit, Great Location, Dog Friendly, Kitchen
3 bedrooms, 3 beds, 1 bathroom
19–24 Aug
4.98 out of 5 average rating, 165 reviews
Guest favourite
Chalet in Stockbridge
Vermont Chalet
2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
4.85 out of 5 average rating, 203 reviews
Top guest favourite
Tiny home in Pittsford
Le Petit Maison d 'Allaire
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.96 out of 5 average rating, 56 reviews
Top guest favourite
Yurt in Randolph
Howling Wolf Farm Yurt--A Magical Glamping Retreat
1 queen bed, WC
23–28 Aug
4.99 out of 5 average rating, 162 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
4.94 out of 5 average rating, 18 reviews
Top guest favourite
Room in Castleton
Room in rural home with lovely mountain views
1 double bed, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 245 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
Guest favourite
Cabin in Brandon
Honeycrisp Cabin
1 bedroom, 1 bed, 1 bathroom
15–20 Aug
4.95 out of 5 average rating, 39 reviews
Top guest favourite
Cottage in Windsor
Ogden's Mill Farm
2 bedrooms, 3 beds, 1 bathroom
16–21 Nov
4.97 out of 5 average rating, 463 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