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Search results; Over 1,000 homes in Pittsfield

Top guest favourite
Cabin in Pittsfield
Tiny Vermont Cabin!
1 bedroom, 1 bed, 1 private bathroom
9–14 Aug
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4.98 out of 5 average rating, 190 reviews
Guest favourite
Home in Pittsfield
Romantic Retreat, Hot Tub, near Killington Mtn
2 bedrooms, 2 beds, 1 bathroom
8–13 Aug
4.94 out of 5 average rating, 50 reviews
Bungalow in Pittsfield
Woodland Retreat ~ Green Mtns ~ Hike Bike Ski
2 bedrooms, 4 beds, 1 bathroom
22–27 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Pittsfield
Skyeburst | Modern Mtn Home
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Aug
4.98 out of 5 average rating, 42 reviews
Guest favourite
Home in Pittsfield
Peak Hill – 3 Bedroom, Hot Tub. Car Charger!
3 bedrooms, 5 beds, 2 bathrooms
1–6 Aug
5.0 out of 5 average rating, 21 reviews
Guest favourite
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
Guest favourite
Home in Pittsfield
VT Cabin, close to Killington Mountain and lakes.
5 bedrooms, 4 beds, 3 bathrooms
1–6 Aug
4.96 out of 5 average rating, 47 reviews
Top guest favourite
Home in Stockbridge
Unique Mountain Retreat
4 bedrooms, 7 beds, 2 bathrooms
1–6 Aug
5.0 out of 5 average rating, 42 reviews
Top guest favourite
Home in Killington
Snowarts- Game room, Fireplace, Close to golf!
3 bedrooms, 7 beds, 2 bathrooms
1–6 Aug
4.97 out of 5 average rating, 79 reviews
Top guest favourite
Flat in Killington
Jack S'Bearo- AC, Pool, Mountain Views, Hiking Gym
1 bedroom, 2 beds, 1 bathroom
2–7 Aug
4.98 out of 5 average rating, 119 reviews
Top guest favourite
Home in Pittsfield
Killington area Inn all to yourself! 9bd/10 bath
9 bedrooms, 14 beds, 10 bathrooms
1–6 Aug
5.0 out of 5 average rating, 52 reviews
Guest favourite
Home in Killington
Entire home- Killington, Vermont Ski, Hike, Bike
3 bedrooms, 4 beds, 2.5 bathrooms
2–7 Aug
5.0 out of 5 average rating, 18 reviews
Guest favourite
Chalet in Stockbridge
Vermont Chalet
2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
4.85 out of 5 average rating, 199 reviews
Top guest favourite
Chalet in Stockbridge
Gnome Home Mountain Ski Chalet w/Sauna Killington
4 bedrooms, 6 beds, 2 bathrooms
2–7 Aug
4.97 out of 5 average rating, 163 reviews
Top guest favourite
Apartment in Killington
Golf Hike 1 bedrm 1 night ok Pico free shuttles
1 bedroom, 3 beds, 1 bathroom
1–6 Aug
4.93 out of 5 average rating, 499 reviews
Guest favourite
Home in Pittsfield
Killington area home - 4 seasons - hot tub and A/C
3 bedrooms, 10 beds, 2.5 bathrooms
16–21 Aug
4.85 out of 5 average rating, 256 reviews
Top guest favourite
Home in Killington
Cedar Wood Lodge
6 bedrooms, 4 bathrooms
9–14 Aug
5.0 out of 5 average rating, 16 reviews
Guest favourite
Home in Pittsfield
Green Mountain/Killington Getaway
3 bedrooms, 6 beds, 2 bathrooms
1–6 Aug
4.84 out of 5 average rating, 88 reviews
Guest favourite
Home in Pittsfield
The Merak Haus – a wooded retreat
3 bedrooms, 8 beds, 2.5 bathrooms
1–6 Aug
5.0 out of 5 average rating, 9 reviews