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Search results; Over 1,000 homes in Pittsfield

Guest favourite
Hotel in Pittsfield
Clear River Inn - 2 Double Beds (2nd Floor)
1 bedroom, 2 beds, 1 private bathroom
1–6 Aug
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4.88 out of 5 average rating, 129 reviews
Top guest favourite
Cabin in Pittsfield
Tiny Vermont Cabin!
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
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
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
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 Stockbridge
Ski Home/Arcade Mountain Views Near Killington/Woo
3 bedrooms, 6 beds, 2.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 22 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
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
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
Guest favourite
Home in Killington
Killington Chalet: Hot Tub, Fireplace, spacious 4b
4 bedrooms, 5 beds, 2 bathrooms
30 Aug – 4 Sept
4.94 out of 5 average rating, 68 reviews
Guest favourite
Home in Pittsfield
The Merak Haus – a wooded retreat
3 bedrooms, 8 beds, 2.5 bathrooms
11–16 Aug
5.0 out of 5 average rating, 9 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
Superhost
Apartment in Killington
Killington Resort Condo | Pool, Sauna & Hot Tub
3 bedrooms, 3 beds, 2 bathrooms
3–8 Aug
New place to stay
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 Pittsfield
Killington area entire Inn to yourself! 14bd/15bth
14 bedrooms, 24 beds, 15 bathrooms
6–11 Aug
5.0 out of 5 average rating, 19 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
Top guest favourite
Cabin in Killington
Green Mountain Yay Frame
3 bedrooms, 3 beds, 3 bathrooms
11–16 Sept
5.0 out of 5 average rating, 83 reviews