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Search results; Over 1,000 homes in Pittsfield

Descriptions are based on details hosts provide
Superhost
Hotel in Pittsfield
Clear River Inn - 2 Double Beds (Ground Floor)
1 bedroom, 2 beds, 1 private bathroom
15–20 Jul
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4.75 out of 5 average rating, 115 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
Top guest favourite
Cabin in Pittsfield
Newly built cabin with a fireplace
1 bedroom, 1 queen bed, 1 bathroom
15–20 Jul
4.98 out of 5 average rating, 188 reviews
Guest favourite
Home in Pittsfield
Architect-designed chalet with vaulted wood ceilings
2 bedrooms, 2 beds, 1 bathroom
25–30 Jul
4.96 out of 5 average rating, 48 reviews
Top guest favourite
Home in Pittsfield
Killington area entire Inn to yourself! 14bd/15bth
14 bedrooms, 24 beds, 15 bathrooms
19–24 Jul
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Home in Pittsfield
A former inn with bar and pool table
9 bedrooms, 14 beds, 10 bathrooms
23–28 Jul
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Home in Stockbridge
Arcade room with mountain views near Killington
3 bedrooms, 6 beds, 2.5 bathrooms
26–31 Jul
5.0 out of 5 average rating, 21 reviews
Guest favourite
Home in Pittsfield
Hot tub and slope views from deck
3 bedrooms, 5 beds, 2 bathrooms
15–20 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
Flat in Killington
Hot tub, sauna, and pool on-site
1 bedroom, 3 beds, 1 bathroom
5–10 Aug
4.89 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
17–22 Jul
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Holiday home in Pittsfield
The Barn Door Lodge
4 bedrooms, 7 beds, 4.5 bathrooms
15–20 Jul
4.9 out of 5 average rating, 63 reviews
Top guest favourite
Apartment in Killington
Cozy Condo - AC & Pool. Close to Golf & Bike
1 bedroom, 2 beds, 1 bathroom
26–31 Jul
4.98 out of 5 average rating, 174 reviews
Top guest favourite
Home in Stockbridge
Unique Mountain Retreat
4 bedrooms, 7 beds, 2 bathrooms
15–20 Jul
5.0 out of 5 average rating, 42 reviews
Guest favourite
Home in Pittsfield
Wood stove and deck overlooking mountain woods
3 bedrooms, 6 beds, 2 bathrooms
15–20 Jul
4.84 out of 5 average rating, 88 reviews
Guest favourite
Hotel in Pittsfield
Renovated inn on scenic Route 100
1 bedroom, 1 king bed, 1 bathroom
16–21 Jul
4.76 out of 5 average rating, 25 reviews
Guest favourite
Home in Pittsfield
Two decks and a fire pit near Killington
5 bedrooms, 4 beds, 3 bathrooms
15–20 Jul
4.96 out of 5 average rating, 47 reviews
Guest favourite
Home in Pittsfield
The Guernsey Brook Cabin
3 bedrooms, 5 beds, 2 bathrooms
15–20 Jul
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Guest suite in Stockbridge
Mountain views with a fire pit
1 bedroom, 1 bed, 1 bathroom
4–9 Aug
5.0 out of 5 average rating, 115 reviews