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Search results; Over 1,000 homes in Stockbridge

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Top guest favourite
Chalet in Stockbridge
Gnome Home Mountain Ski Chalet w/Sauna Killington
4 bedrooms, 6 beds, 2 private bathrooms
16–21 Oct
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4.97 out of 5 average rating, 165 reviews
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Top guest favourite
Home in Stockbridge
Riverfront Retreat in Stockbridge
3 bedrooms, 4 beds, 1.5 bathrooms
16–21 Oct
5.0 out of 5 average rating, 42 reviews
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Guest favourite
Chalet in Stockbridge
BENT TREE Vermont, Mtn Chalet 25 min to Killington
4 bedrooms, 7 beds, 3.5 bathrooms
1–6 Oct
4.94 out of 5 average rating, 50 reviews
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Top guest favourite
Guest suite in Stockbridge
Studio Suite with Vermont Style & Amazing Views
1 bedroom, 1 bed, 1 bathroom
23–28 Oct
5.0 out of 5 average rating, 118 reviews
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Guest favourite
Cabin in Stockbridge
RZEKA Cottage: Riverfront home in the Green mts.
3 bedrooms, 4 beds, 2 bathrooms
13–18 Oct
4.94 out of 5 average rating, 69 reviews
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Guest favourite
Chalet in Stockbridge
Vermont Chalet
2 bedrooms, 2 beds, 1 bathroom
25–30 Oct
4.86 out of 5 average rating, 210 reviews
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Top guest favourite
Home in Stockbridge
Unique Mountain Retreat
4 bedrooms, 7 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 42 reviews
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Guest favourite
Home in Stockbridge
1800s Farmhouse with River Access. Private w/ Land
3 bedrooms, 3 beds, 2 bathrooms
13–18 Oct
4.95 out of 5 average rating, 38 reviews
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Chalet in Stockbridge
Perfect, private chalet! Ski, bike, hike, 100mbps
6 bedrooms, 10 beds, 3 bathrooms
1–6 Oct
4.9 out of 5 average rating, 21 reviews
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Guest favourite
Home in Pittsfield
VT Cabin, close to Killington Mountain and lakes.
5 bedrooms, 4 beds, 3 bathrooms
1–6 Oct
4.96 out of 5 average rating, 49 reviews
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Guest favourite
Home in Stockbridge
Ski Home/Arcade Mountain Views Near Killington/Woo
3 bedrooms, 6 beds, 2.5 bathrooms
12–18 Oct
5.0 out of 5 average rating, 22 reviews
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Guest favourite
Home in Pittsfield
Green Mountain/Killington Getaway
3 bedrooms, 6 beds, 2 bathrooms
1–6 Oct
4.84 out of 5 average rating, 88 reviews
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Home in Pittsfield
Green Mountain Farmhouse | 7 Miles to Killington
3 bedrooms, 4 beds, 2.5 bathrooms
19–24 Oct
5.0 out of 5 average rating, 7 reviews
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Superhost
Flat in Killington
Private 9 Bedroom Guesthouse - The Trailside Inn
9 bedrooms, 9 beds, 4 bathrooms
19–24 Oct
5.0 out of 5 average rating, 14 reviews
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Guest favourite
Cabin in Stockbridge
North Country Cabin - Private Mountain Retreat
4 bedrooms, 8 beds, 3 bathrooms
1–6 Oct
4.96 out of 5 average rating, 27 reviews
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Guest favourite
Home in Pittsfield
Killington area entire Inn to yourself! 14bd/15bth
14 bedrooms, 24 beds, 15 bathrooms
4–9 Oct
4.95 out of 5 average rating, 21 reviews
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Guest favourite
Home in Killington
Killington Mountain Farmhouse-5 min to Skiing
4 bedrooms, 8 beds, 3 bathrooms
6–11 Oct
4.88 out of 5 average rating, 26 reviews
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Top guest favourite
Cabin in Stockbridge
1958 Classic "Hunting Cabin" w/ Breathtaking Views
1 bedroom, 1 double bed, 1 bathroom
1–6 May
4.94 out of 5 average rating, 136 reviews
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Top guest favourite
Holiday home in Pittsfield
The Barn Door Lodge
4 bedrooms, 7 beds, 4.5 bathrooms
1–6 Oct
4.91 out of 5 average rating, 64 reviews