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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
10–15 Aug
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4.88 out of 5 average rating, 129 reviews
Top guest favourite
Cabin in Pittsfield
Tiny Vermont Cabin!
1 bedroom, 1 queen bed, 1 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, 4 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
10–15 Aug
5.0 out of 5 average rating, 21 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
10–15 Aug
5.0 out of 5 average rating, 116 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
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, 55 reviews
Top guest favourite
Earthen home in Granville
Sculpted Earthen Yurt in Green Mtns
3 bedrooms, 4 beds, 1 bathroom
10–15 Sept
4.93 out of 5 average rating, 175 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
Riverside Retreat: Hike & Bike From Your Doorstep
3 bedrooms, 6 beds, 2.5 bathrooms
10–15 Aug
4.95 out of 5 average rating, 63 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
Yurt in Randolph
Howling Wolf Farm Yurt--A Magical Glamping Retreat
1 queen bed, WC
11–16 Aug
4.99 out of 5 average rating, 161 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
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
Home in Pittsfield
Killington area home - 4 seasons - hot tub and A/C
3 bedrooms, 11 beds, 2.5 bathrooms
16–21 Aug
4.85 out of 5 average rating, 256 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