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Search results; Over 1,000 homes in Stockbridge

Top guest favourite
Cabin in Stockbridge
1958 Classic "Hunting Cabin" w/ Breathtaking Views
1 bedroom, 1 bed, 1 private bathroom
1–6 May
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4.94 out of 5 average rating, 135 reviews
Top guest favourite
Guest suite in Stockbridge
Studio Suite with Vermont Style & Amazing Views
1 bedroom, 1 bed, 1 bathroom
21–26 Sept
5.0 out of 5 average rating, 117 reviews
Guest favourite
Chalet in Stockbridge
Vermont Chalet
2 bedrooms, 2 beds, 1 bathroom
3–8 Nov
4.86 out of 5 average rating, 208 reviews
Top guest favourite
Home in Stockbridge
Riverfront Retreat in Stockbridge
3 bedrooms, 4 beds, 1.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 41 reviews
Top guest favourite
Chalet in Stockbridge
Gnome Home Mountain Ski Chalet w/Sauna Killington
4 bedrooms, 6 beds, 2 bathrooms
20–25 Sept
4.97 out of 5 average rating, 165 reviews
Guest favourite
Home in Pittsfield
The Merak Haus – a wooded retreat
3 bedrooms, 8 beds, 2.5 bathrooms
16–21 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Chalet in Stockbridge
BENT TREE Vermont, Mtn Chalet 25 min to Killington
4 bedrooms, 7 beds, 3.5 bathrooms
14–19 Sept
4.94 out of 5 average rating, 50 reviews
Guest favourite
Home in Stockbridge
Ski Home/Arcade Mountain Views Near Killington/Woo
3 bedrooms, 6 beds, 2.5 bathrooms
14–20 Sept
5.0 out of 5 average rating, 22 reviews
Guest favourite
Home in Stockbridge
1800s Farmhouse with River Access. Private w/ Land
3 bedrooms, 3 beds, 2 bathrooms
25–30 Sept
4.95 out of 5 average rating, 38 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
Guest favourite
Cabin in Stockbridge
RZEKA Cottage: Riverfront home in the Green mts.
3 bedrooms, 4 beds, 2 bathrooms
24–29 Sept
4.96 out of 5 average rating, 68 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 Stockbridge
Unique Mountain Retreat
4 bedrooms, 7 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 42 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
Green Mountain/Killington Getaway
3 bedrooms, 6 beds, 2 bathrooms
14–19 Sept
4.84 out of 5 average rating, 88 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 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
Guest favourite
Cabin in Stockbridge
North Country Cabin - Private Mountain Retreat
4 bedrooms, 8 beds, 3 bathrooms
15–20 Sept
4.96 out of 5 average rating, 27 reviews
Top guest favourite
Apartment in Killington
Cozy Condo - Close to Ski, Golf & Bike
1 bedroom, 2 beds, 1 bathroom
1–6 Nov
4.98 out of 5 average rating, 188 reviews