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Search results; Over 1,000 homes in Pittsfield

Top guest favourite
Holiday home in Pittsfield
The Barn Door Lodge
4 bedrooms, 7 beds, 4.5 private bathrooms
20–25 Aug
,
4.91 out of 5 average rating, 64 reviews
Guest favourite
Cabin in Pittsfield
Tiny Vermont Cabin!
1 bedroom, 1 queen bed
30 Aug – 4 Sept
4.98 out of 5 average rating, 194 reviews
Guest favourite
Home in Pittsfield
Romantic Retreat, Hot Tub, near Killington Mtn
2 bedrooms, 2 beds
1–6 Sept
4.94 out of 5 average rating, 52 reviews
Guest favourite
Bungalow in Pittsfield
Woodland Acres ~ Green Mtns ~ Hike Bike Ski
2 bedrooms, 4 beds
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
24–29 Aug
4.98 out of 5 average rating, 43 reviews
Home in Pittsfield
Post & Beam Vermont Farmhouse | Near Killington
3 bedrooms, 4 beds
4–9 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Guest suite in Stockbridge
Studio Suite with Vermont Style & Amazing Views
1 bedroom, 1 bed
23–28 Aug
5.0 out of 5 average rating, 116 reviews
Guest favourite
Home in Pittsfield
Killington area home - 4 seasons - hot tub and A/C
3 bedrooms, 11 beds
20–25 Aug
4.85 out of 5 average rating, 256 reviews
Top guest favourite
Home in Pittsfield
NEW 3BR Home: Hot Tub, AC, EV & Lift Ticket Deals
3 bedrooms, 7 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Pittsfield
Peak Hill – 3 Bedroom, Hot Tub. Car Charger!
3 bedrooms, 5 beds
20–25 Aug
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Earthen home in Granville
Sculpted Earthen Yurt in Green Mtns
3 bedrooms, 4 beds
13–18 Sept
4.93 out of 5 average rating, 177 reviews
Guest favourite
Cabin in Brandon
Honeycrisp Cabin
1 bedroom, 1 bed
14–19 Sept
4.95 out of 5 average rating, 40 reviews
Top guest favourite
Cottage in Windsor
Ogden's Mill Farm
2 bedrooms, 3 beds
16–21 Nov
4.97 out of 5 average rating, 464 reviews
Home in Rochester
Iron Springs Cabin (Black Haus 2.0)
1 bedroom, 1 queen bed
26–31 Oct
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Pittsfield
Trailside Retreat: Hike & Bike From Your Doorstep
3 bedrooms, 6 beds
24–29 Aug
4.95 out of 5 average rating, 64 reviews
Top guest favourite
Yurt in Randolph
Howling Wolf Farm Yurt--A Magical Glamping Retreat
1 queen bed
31 Aug – 5 Sept
4.99 out of 5 average rating, 162 reviews
Top guest favourite
Room in Castleton
Room in rural home with lovely mountain views
1 double bed
23–28 Aug
5.0 out of 5 average rating, 247 reviews
Top guest favourite
Home in Mendon
New Firepit, Great Location, Dog Friendly, Kitchen
3 bedrooms, 3 beds
30 Aug – 4 Sept
4.98 out of 5 average rating, 168 reviews
Top guest favourite
Flat in Pittsford
Fox Farm · Hilltop Retreat Near Mountains & Lakes
2 bedrooms, 2 queen beds
21–26 Aug
5.0 out of 5 average rating, 29 reviews