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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
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
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
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
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
Flat in Killington
Jack S'Bearo- AC, Pool, Mountain Views, Hiking Gym
4.98 out of 5 average rating, 119 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Cabin in Bethel
Phoebe’s Perch
5.0 out of 5 average rating, 19 reviews, 1 bedroom, 3 beds, WC
16–21 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
Guest favourite
Home in Stockbridge
Ski Home/Arcade Mountain Views Near Killington/Woo
5.0 out of 5 average rating, 22 reviews, 3 bedrooms, 6 beds, 2.5 bathrooms
16–21 Aug
Guest favourite
Home in Stockbridge
Little House on the Green
5.0 out of 5 average rating, 13 reviews, 1 bedroom, 4 beds, 1 bathroom
2–7 Apr
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
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
Top guest favourite
Home in Stockbridge
Riverfront Retreat in Stockbridge
5.0 out of 5 average rating, 32 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
2–7 Aug
Top guest favourite
Guest suite in Stockbridge
Studio Suite with Vermont Style & Amazing Views
5.0 out of 5 average rating, 115 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Aug
Top guest favourite
Flat in Killington
Birch Hollow- Pool, Hot tub, Gym, Sauna!
4.94 out of 5 average rating, 16 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
Top guest favourite
Apartment in Killington
Bright Ski on/off Condo Full Kitchen-Free Shuttle!
4.95 out of 5 average rating, 214 reviews, 2 beds, 1 bathroom
9–14 Aug
Guest favourite
Apartment in Killington
Fresh Tracks - 3 Bed Studio, Heated Saltwater Pool
4.86 out of 5 average rating, 7 reviews, 1 bedroom, 3 beds, 1 bathroom
1–6 Aug
Top guest favourite
Room in Mendon
Private fireplace suite & luxury bath - Killington
4.99 out of 5 average rating, 829 reviews, 1 queen bed, 1 bathroom
10–15 Aug
Home in Killington
Trails End Condo at Trail Creek
New place to stay, 1 bedroom, 2 beds, 1 bathroom
1–6 Aug