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Search results; Over 1,000 homes in Pittsfield

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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
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Top guest favourite
Home in Pittsfield
Skyeburst | Modern Mtn Home
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Sept
4.98 out of 5 average rating, 44 reviews
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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, 53 reviews
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Guest favourite
Home in Pittsfield
Peak Hill – 3 Bedroom, Hot Tub. Car Charger!
3 bedrooms, 5 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 23 reviews
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Top guest favourite
Home in Pittsfield
Killington area Inn all to yourself! 9bd/10 bath
9 bedrooms, 14 beds, 10 bathrooms
1–6 Sept
5.0 out of 5 average rating, 52 reviews
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Top guest favourite
Bungalow in Pittsfield
Woodland Acres ~ Green Mtns ~ Hike Bike Ski
2 bedrooms, 4 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 6 reviews
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Guest favourite
Home in Pittsfield
Trailside Retreat: Hike & Bike From Your Doorstep
3 bedrooms, 6 beds, 2.5 bathrooms
7–12 Sept
4.95 out of 5 average rating, 64 reviews
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Guest favourite
Home in Pittsfield
Mountain Top - Fresh Pond - Killington - Hot Tub
4 bedrooms, 9 beds, 3.5 bathrooms
7–12 Sept
4.95 out of 5 average rating, 40 reviews
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Guest favourite
Home in Pittsfield
Killington area home - 4 seasons - hot tub and A/C
3 bedrooms, 11 beds, 2.5 bathrooms
12–17 Sept
4.85 out of 5 average rating, 256 reviews
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Guest favourite
Home in Pittsfield
Killington area entire Inn to yourself! 14bd/15bth
14 bedrooms, 24 beds, 15 bathrooms
1–6 Sept
4.95 out of 5 average rating, 21 reviews
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Superhost
Home in Pittsfield
NEW 3BR Home: Hot Tub, AC, EV & Lift Ticket Deals
3 bedrooms, 7 beds, 3 bathrooms
6–11 Sept
5.0 out of 5 average rating, 18 reviews
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Superhost
Home in Stockbridge
Ski/MTB/Arcade/Pool Table near Killington/Pico/Sug
6 bedrooms, 10 beds, 5 bathrooms
4–9 Sept
4.92 out of 5 average rating, 13 reviews
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Guest favourite
Home in Pittsfield
Green Mountain/Killington Getaway
3 bedrooms, 6 beds, 2 bathrooms
1–6 Sept
4.84 out of 5 average rating, 88 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 Sept
4.91 out of 5 average rating, 64 reviews
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Guest favourite
Home in Pittsfield
The Merak Haus – a wooded retreat
3 bedrooms, 8 beds, 2.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Home in Pittsfield
The Fiddlehead Lodge (Green Mountain Getaway)
4 bedrooms, 9 beds, 1.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 14 reviews
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Home in Pittsfield
A million-dollar view near Killington on 60 acres.
4 bedrooms, 6 beds, 1.5 bathrooms
6–11 May
4.83 out of 5 average rating, 119 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 Sept
4.96 out of 5 average rating, 49 reviews