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Search results; Over 1,000 homes in Pittsfield

Guest favourite
Home in Pittsfield
A million-dollar view near Killington on 60 acres.
4 bedrooms, 6 beds, 1.5 private bathrooms
6–11 May
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4.83 out of 5 average rating, 119 reviews
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, 194 reviews
Guest favourite
Home in Pittsfield
Romantic Retreat, Hot Tub, near Killington Mtn
2 bedrooms, 2 beds, 1 bathroom
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, 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
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, 2.5 bathrooms
4–9 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Pittsfield
Peak Hill – 3 Bedroom, Hot Tub. Car Charger!
3 bedrooms, 5 beds, 2 bathrooms
20–25 Aug
5.0 out of 5 average rating, 23 reviews
Guest favourite
Home in Pittsfield
Killington area home - 4 seasons - hot tub and A/C
3 bedrooms, 11 beds, 2.5 bathrooms
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, 3 bathrooms
20–25 Aug
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Guest suite in Stockbridge
Studio Suite with Vermont Style & Amazing Views
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 116 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, 4 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, 464 reviews
Top guest favourite
Rooms in Mendon
Cozy private room - Killington
2 bedrooms, 1 queen bed, 1 bathroom
20–25 Aug
4.98 out of 5 average rating, 596 reviews
Guest favourite
Cabin in Bethel
The Gourmet Cabin at Stitchdown Farm
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.95 out of 5 average rating, 109 reviews
Top guest favourite
Room in Danby
Spectacular view, private bathroom. One king bed
1 king bed, 1.5 bathrooms
23–28 Aug
4.99 out of 5 average rating, 237 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, 36 reviews
Top guest favourite
Home in Mendon
New Firepit, Great Location, Dog Friendly, Kitchen
3 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 168 reviews
Top guest favourite
Home in Pittsfield
Killington area Inn all to yourself! 9bd/10 bath
9 bedrooms, 14 beds, 10 bathrooms
20–25 Aug
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Yurt in Pittsford
Remote Cozy Yurt with Sunset Views
1 bedroom, 3 beds, 1.5 bathrooms
23–28 Aug
4.97 out of 5 average rating, 171 reviews