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Search results; Over 1,000 homes in Pittsfield

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Top guest favourite
Holiday home in Pittsfield
The Barn Door Lodge
4 bedrooms, 7 beds, 4.5 private bathrooms
16–21 Sept
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4.91 out of 5 average rating, 64 reviews
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Home in Pittsfield
Green Mountain Farmhouse | 7 Miles to Killington
3 bedrooms, 4 beds
17–22 Sept
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Home in Pittsfield
Skyeburst | Modern Mtn Home
3 bedrooms, 3 beds
20–25 Sept
4.98 out of 5 average rating, 45 reviews
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Top guest favourite
Home in Pittsfield
Trailside Retreat: Hike & Bike From Your Doorstep
3 bedrooms, 6 beds
20–25 Sept
4.95 out of 5 average rating, 65 reviews
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Top guest favourite
Home in Pittsfield
Woodland Acres ~ Green Mtns ~ Hike Bike Ski
2 bedrooms, 4 beds
27 Oct – 1 Nov
5.0 out of 5 average rating, 8 reviews
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Guest favourite
Home in Pittsfield
Romantic Retreat, Hot Tub, near Killington Mtn
2 bedrooms, 2 beds
16–21 Oct
4.93 out of 5 average rating, 56 reviews
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Guest favourite
Chalet in Pittsfield
Four season Killington/Pico area chalet
3 bedrooms, 6 beds
7–12 Dec
4.78 out of 5 average rating, 95 reviews
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Guest favourite
Home in Pittsfield
Killington area home - 4 seasons - hot tub and A/C
3 bedrooms, 11 beds
21–26 Sept
4.85 out of 5 average rating, 256 reviews
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Guest favourite
Home in Pittsfield
Green Mountain/Killington Getaway
3 bedrooms, 6 beds
16–21 Sept
4.84 out of 5 average rating, 88 reviews
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Guest favourite
Home in Pittsfield
VT Cabin, close to Killington Mountain and lakes.
5 bedrooms, 4 beds
16–21 Sept
4.96 out of 5 average rating, 49 reviews
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Guest favourite
Home in Pittsfield
Killington area entire Inn to yourself! 14bd/15bth
14 bedrooms, 24 beds
20–25 Sept
4.95 out of 5 average rating, 21 reviews
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Guest favourite
Home in Pittsfield
The Merak Haus – a wooded retreat
3 bedrooms, 8 beds
18–23 Sept
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Home in Pittsfield
Killington area Inn all to yourself! 9bd/10 bath
9 bedrooms, 14 beds
16–21 Sept
5.0 out of 5 average rating, 52 reviews
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Top guest favourite
Home in Pittsfield
NEW 3BR Home: Hot Tub, AC, EV & Lift Ticket Deals
3 bedrooms, 7 beds
20–25 Sept
5.0 out of 5 average rating, 20 reviews
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Guest favourite
Home in Pittsfield
Peak Hill – 3 Bedroom, Hot Tub. Car Charger!
3 bedrooms, 5 beds
20–25 Sept
5.0 out of 5 average rating, 23 reviews
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Home in Pittsfield
Hideaway Mountain at Killington
3 bedrooms, 4 beds
17–22 Sept
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Home in Rochester
The Amee Farm Lodge
15 bedrooms, 18 beds
26–31 Oct
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Guest favourite
Home in Pittsfield
A million-dollar view near Killington on 60 acres.
4 bedrooms, 6 beds
6–11 May
4.83 out of 5 average rating, 119 reviews
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Top guest favourite
Home in Pittsfield
The Fiddlehead Lodge (Green Mountain Getaway)
4 bedrooms, 9 beds
16–21 Sept
5.0 out of 5 average rating, 14 reviews