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Search results; Over 1,000 homes in Pittsfield

Top guest favourite
Holiday home in Pittsfield
The Barn Door Lodge
4 bedrooms, 7 beds, 4.5 private bathrooms
10–15 Aug
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4.91 out of 5 average rating, 64 reviews
Top guest favourite
Cabin in Pittsfield
Tiny Vermont Cabin!
4.98 out of 5 average rating, 190 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Bungalow in Pittsfield
Woodland Retreat ~ Green Mtns ~ Hike Bike Ski
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 4 beds, 1 bathroom
22–27 Aug
Guest favourite
Home in Pittsfield
Romantic Retreat, Hot Tub, near Killington Mtn
4.94 out of 5 average rating, 50 reviews, 2 bedrooms, 2 beds, 1 bathroom
8–13 Aug
Top guest favourite
Home in Pittsfield
Skyeburst | Modern Mtn Home
4.98 out of 5 average rating, 42 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Aug
Guest favourite
Home in Pittsfield
Post & Beam Vermont Farmhouse | Near Killington
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
7–12 Sept
Guest favourite
Home in Pittsfield
Peak Hill – 3 Bedroom, Hot Tub. Car Charger!
5.0 out of 5 average rating, 21 reviews, 3 bedrooms, 5 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Home in Pittsfield
Killington area Inn all to yourself! 9bd/10 bath
5.0 out of 5 average rating, 52 reviews, 9 bedrooms, 14 beds, 10 bathrooms
1–6 Aug
Guest favourite
Home in Pittsfield
VT Cabin, close to Killington Mountain and lakes.
4.96 out of 5 average rating, 47 reviews, 5 bedrooms, 4 beds, 3 bathrooms
1–6 Aug
Guest favourite
Home in Pittsfield
Riverside Retreat: Hike & Bike From Your Doorstep
4.95 out of 5 average rating, 63 reviews, 3 bedrooms, 6 beds, 2.5 bathrooms
9–14 Aug
Top guest favourite
Home in Stockbridge
Unique Mountain Retreat
5.0 out of 5 average rating, 42 reviews, 4 bedrooms, 7 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Home in Killington
Cedar Wood Lodge
5.0 out of 5 average rating, 16 reviews, 6 bedrooms, 4 bathrooms
9–14 Aug
Guest favourite
Home in Pittsfield
Killington area home - 4 seasons - hot tub and A/C
4.85 out of 5 average rating, 256 reviews, 3 bedrooms, 10 beds, 2.5 bathrooms
16–21 Aug
Guest favourite
Home in Pittsfield
The Merak Haus – a wooded retreat
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 8 beds, 2.5 bathrooms
1–6 Aug
Top guest favourite
Home in Pittsfield
Killington area entire Inn to yourself! 14bd/15bth
5.0 out of 5 average rating, 19 reviews, 14 bedrooms, 24 beds, 15 bathrooms
6–11 Aug
Top guest favourite
Home in Killington
Snowarts- Game room, Fireplace, Close to golf!
4.97 out of 5 average rating, 79 reviews, 3 bedrooms, 7 beds, 2 bathrooms
1–6 Aug
Guest favourite
Home in Killington
Entire home- Killington, Vermont Ski, Hike, Bike
5.0 out of 5 average rating, 18 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
2–7 Aug
Top guest favourite
Chalet in Stockbridge
Gnome Home Mountain Ski Chalet w/Sauna Killington
4.97 out of 5 average rating, 163 reviews, 4 bedrooms, 6 beds, 2 bathrooms
2–7 Aug
Guest favourite
Home in Pittsfield
Green Mountain/Killington Getaway
4.84 out of 5 average rating, 88 reviews, 3 bedrooms, 6 beds, 2 bathrooms
1–6 Aug