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Search results; Over 1,000 homes in Pittsfield

Chalet in Pittsfield
Luxury Heart of VT Green Mountains
3 bedrooms, 4 beds, 3.5 private bathrooms
16–21 Jul
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4.95 out of 5 average rating, 57 reviews
Top guest favourite
Cabin in Pittsfield
Tiny Vermont Cabin!
1 bedroom, 1 queen bed, 1 bathroom
25–30 Jul
4.98 out of 5 average rating, 188 reviews
Bungalow in Pittsfield
Woodland Retreat ~ Green Mtns ~ Hike Bike Ski
2 bedrooms, 4 beds, 1 bathroom
29 Jul – 3 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Pittsfield
Romantic Retreat, Hot Tub, near Killington Mtn
2 bedrooms, 2 beds, 1 bathroom
25–30 Jul
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
18–23 Jul
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Pittsfield
Post & Beam Vermont Farmhouse | Near Killington
3 bedrooms, 4 beds, 2.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Pittsfield
Killington area Inn all to yourself! 9bd/10 bath
9 bedrooms, 14 beds, 10 bathrooms
23–28 Jul
5.0 out of 5 average rating, 52 reviews
Guest favourite
Home in Pittsfield
Peak Hill – 3 Bedroom, Hot Tub. Car Charger!
3 bedrooms, 5 beds, 2 bathrooms
16–21 Jul
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Home in Pittsfield
Skyeburst | Modern Mtn Home
3 bedrooms, 3 beds, 2.5 bathrooms
19–24 Jul
4.98 out of 5 average rating, 40 reviews
Top guest favourite
Home in Stockbridge
Ski Home/Arcade Mountain Views Near Killington/Woo
3 bedrooms, 6 beds, 2.5 bathrooms
26–31 Jul
5.0 out of 5 average rating, 22 reviews
Guest favourite
Home in Pittsfield
Green Mountain/Killington Getaway
3 bedrooms, 6 beds, 2 bathrooms
16–21 Jul
4.84 out of 5 average rating, 88 reviews
Guest favourite
Cabin in Goshen
The Berghüttli: Glowing Swiss Hut in the Forest
2 bedrooms, 2 beds, 1 bathroom
19–24 Jul
4.97 out of 5 average rating, 141 reviews
Guest favourite
Home in Killington
Killington Chalet: Hot Tub, Fireplace, spacious 4b
4 bedrooms, 5 beds, 2 bathrooms
24–29 Aug
4.94 out of 5 average rating, 66 reviews
Guest favourite
Home in Pittsfield
VT Cabin, close to Killington Mountain and lakes.
5 bedrooms, 4 beds, 3 bathrooms
16–21 Jul
4.96 out of 5 average rating, 47 reviews
Top guest favourite
Cabin in Leicester
Log Cabin Getaway near Middlebury and Green Mtns
2 bedrooms, 3 beds, 1 bathroom
11–16 Aug
4.98 out of 5 average rating, 876 reviews
Top guest favourite
Home in Killington
Hot tub|Sauna|Movie Room! 8 min to Killington Mtn!
4 bedrooms, 7 beds, 4 bathrooms
8–13 Aug
5.0 out of 5 average rating, 50 reviews
Guest favourite
Chalet in Stockbridge
Vermont Chalet
2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
4.85 out of 5 average rating, 197 reviews
Top guest favourite
Home in Killington
Snowarts- Game room, Fireplace, Close to golf!
3 bedrooms, 7 beds, 2 bathrooms
16–21 Jul
4.97 out of 5 average rating, 78 reviews
Top guest favourite
Holiday home in Pittsfield
The Barn Door Lodge
4 bedrooms, 7 beds, 4.5 bathrooms
16–21 Jul
4.9 out of 5 average rating, 63 reviews