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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
25–30 Jul
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4.98 out of 5 average rating, 189 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
Guest favourite
Home in Pittsfield
Romantic Retreat, Hot Tub, near Killington Mtn
4.96 out of 5 average rating, 49 reviews, 2 bedrooms, 2 beds, 1 bathroom
8–13 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
22–27 Jul
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
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
23–28 Jul
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
26–31 Jul
Top guest favourite
Home in Pittsfield
Skyeburst | Modern Mtn Home
4.98 out of 5 average rating, 40 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
26–31 Jul
Guest favourite
Home in Killington
NewMont Lodge- Pool, Tennis court, pool table
4.78 out of 5 average rating, 18 reviews, 3 bedrooms, 8 beds, 3 bathrooms
26–31 Jul
Top guest favourite
Home in Stockbridge
Unique Mountain Retreat
5.0 out of 5 average rating, 42 reviews, 4 bedrooms, 7 beds, 2 bathrooms
20–25 Jul
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
26–31 Jul
Home in Ludlow
Large Luxury 6br Okemo Home | Hot Tub | Mtn View
New place to stay, 6 bedrooms, 12 beds, 4.5 bathrooms
27 Jul – 1 Aug
Top guest favourite
Cabin in Leicester
Log Cabin Getaway near Middlebury and Green Mtns
4.98 out of 5 average rating, 876 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
Guest favourite
Home in Pittsfield
Peak Hill – 3 Bedroom, Hot Tub. Car Charger!
5.0 out of 5 average rating, 20 reviews, 3 bedrooms, 5 beds, 2 bathrooms
26–31 Jul
Top guest favourite
Home in Killington
Hot tub|Sauna|Movie Room! 8 min to Killington Mtn!
5.0 out of 5 average rating, 50 reviews, 4 bedrooms, 7 beds, 4 bathrooms
8–13 Aug
Top guest favourite
Holiday home in Pittsfield
The Barn Door Lodge
4.9 out of 5 average rating, 63 reviews, 4 bedrooms, 7 beds, 4.5 bathrooms
20–25 Jul
Guest favourite
Cabin in Goshen
The Berghüttli: Glowing Swiss Hut in the Forest
4.97 out of 5 average rating, 142 reviews, 2 bedrooms, 2 beds, 1 bathroom
29 Aug – 3 Sept
Top guest favourite
Home in Killington
Snowarts- Game room, Fireplace, Close to golf!
4.97 out of 5 average rating, 78 reviews, 3 bedrooms, 7 beds, 2 bathrooms
20–25 Jul
Top guest favourite
Home in Killington
Cedar Wood Lodge
5.0 out of 5 average rating, 16 reviews, 6 bedrooms, 4 bathrooms
21–26 Jul