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Search results; Over 1,000 homes in Pittsfield

Guest favourite
Cabin in Pittsfield
Tiny Vermont Cabin!
1 bedroom, 1 bed, 1 private bathroom
24–29 Oct
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4.98 out of 5 average rating, 195 reviews
Top guest favourite
Home in Pittsfield
Woodland Acres ~ Green Mtns ~ Hike Bike Ski
2 bedrooms, 4 beds, 1 bathroom
11–16 Oct
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Pittsfield
Romantic Retreat, Hot Tub, near Killington Mtn
2 bedrooms, 2 beds, 1 bathroom
21–26 Sept
4.93 out of 5 average rating, 56 reviews
Home in Pittsfield
Green Mountain Farmhouse | 7 Miles to Killington
3 bedrooms, 4 beds, 2.5 bathrooms
17–22 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Pittsfield
Trailside Retreat: Hike & Bike From Your Doorstep
3 bedrooms, 6 beds, 2.5 bathrooms
20–25 Sept
4.95 out of 5 average rating, 65 reviews
Top guest favourite
Home in Pittsfield
Skyeburst | Modern Mtn Home
3 bedrooms, 3 beds, 2.5 bathrooms
20–25 Sept
4.98 out of 5 average rating, 45 reviews
Top guest favourite
Home in Stockbridge
Unique Mountain Retreat
4 bedrooms, 7 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 42 reviews
Guest favourite
Home in Pittsfield
VT Cabin, close to Killington Mountain and lakes.
5 bedrooms, 4 beds, 3 bathrooms
13–18 Sept
4.96 out of 5 average rating, 49 reviews
Guest favourite
Home in Pittsfield
The Merak Haus – a wooded retreat
3 bedrooms, 8 beds, 2.5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Pittsfield
Chalet Suite | 2BR+Loft (15 min to Killington Mtn)
2 bedrooms, 4 beds, 1 bathroom
21–26 Sept
4.97 out of 5 average rating, 30 reviews
Superhost
Hotel in Pittsfield
Clear River Inn - 1 King Bed (2nd Floor)
1 bedroom, 1 king bed, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Pittsfield
NEW 3BR Home: Hot Tub, AC, EV & Lift Ticket Deals
3 bedrooms, 7 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 20 reviews
Guest favourite
Home in Stockbridge
Ski Home/Arcade Mountain Views Near Killington/Woo
3 bedrooms, 6 beds, 2.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 22 reviews
Guest favourite
Home in Pittsfield
Green Mountain/Killington Getaway
3 bedrooms, 6 beds, 2 bathrooms
13–18 Sept
4.84 out of 5 average rating, 88 reviews
Guest favourite
Home in Pittsfield
Peak Hill – 3 Bedroom, Hot Tub. Car Charger!
3 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
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
13–18 Sept
4.85 out of 5 average rating, 256 reviews
Guest favourite
Chalet in Stockbridge
BENT TREE Vermont, Mtn Chalet 25 min to Killington
4 bedrooms, 7 beds, 3.5 bathrooms
13–18 Sept
4.94 out of 5 average rating, 50 reviews
Top guest favourite
Holiday home in Pittsfield
The Barn Door Lodge
4 bedrooms, 7 beds, 4.5 bathrooms
13–18 Sept
4.91 out of 5 average rating, 64 reviews
Guest favourite
Home in Pittsfield
Killington area entire Inn to yourself! 14bd/15bth
14 bedrooms, 24 beds, 15 bathrooms
13–18 Sept
4.95 out of 5 average rating, 21 reviews