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Search results; Over 1,000 homes in Pittsfield

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Hotel in Pittsfield
Clear River Inn - 2 Double Beds (Ground Floor)
1 bedroom, 2 beds, 1 private bathroom
14–19 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
Tiny Vermont Cabin!
1 bedroom, 1 queen bed, 1 bathroom
14–19 Jul
4.98 out of 5 average rating, 188 reviews
Guest favourite
Home in Pittsfield
Romantic Retreat, Hot Tub, near Killington Mtn
2 bedrooms, 2 beds, 1 bathroom
25–30 Jul
4.96 out of 5 average rating, 48 reviews
Guest favourite
Home in Pittsfield
The Merak Haus – a wooded retreat
3 bedrooms, 8 beds, 2.5 bathrooms
15–20 Jul
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Pittsfield
Post & Beam Vermont Farmhouse | Near Killington
3 bedrooms, 4 beds, 2.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Stockbridge
Ski Home/Arcade Mountain Views Near Killington/Woo
3 bedrooms, 6 beds, 2.5 bathrooms
26–31 Jul
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Killington
Hot tub|Sauna|Movie Room! 8 min to Killington Mtn!
4 bedrooms, 7 beds, 4 bathrooms
8–13 Aug
5.0 out of 5 average rating, 50 reviews
Guest favourite
Home in Pittsfield
VT Cabin, close to Killington Mountain and lakes.
5 bedrooms, 4 beds, 3 bathrooms
14–19 Jul
4.96 out of 5 average rating, 47 reviews
Guest favourite
Home in Pittsfield
Peak Hill – 3 Bedroom, Hot Tub. Car Charger!
3 bedrooms, 5 beds, 2 bathrooms
14–19 Jul
5.0 out of 5 average rating, 20 reviews
Guest favourite
Home in Killington
Killington Mountain Farmhouse-5 min to Skiing
4 bedrooms, 8 beds, 3 bathrooms
20–25 Jul
4.85 out of 5 average rating, 20 reviews
Top guest favourite
Flat in Killington
SnowDen- Pool, Gym, Hiking, Fireplace!
3 bedrooms, 5 beds, 2 bathrooms
14–19 Jul
4.98 out of 5 average rating, 43 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
Holiday home in Pittsfield
The Barn Door Lodge
4 bedrooms, 7 beds, 4.5 bathrooms
14–19 Jul
4.9 out of 5 average rating, 63 reviews
Top guest favourite
Home in Killington
Cedar Wood Lodge
6 bedrooms, 4 bathrooms
21–26 Jul
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Pittsfield
Killington area Inn all to yourself! 9bd/10 bath
9 bedrooms, 14 beds, 10 bathrooms
23–28 Jul
5.0 out of 5 average rating, 52 reviews
Guest favourite
Home in Killington
Killington Condo Near Mountain Biking Trails
2 bedrooms, 5 beds, 2 bathrooms
14–19 Jul
4.94 out of 5 average rating, 63 reviews
Top guest favourite
Home in Killington
Beartopia- Hot Tub, Views, 2 Primary Suites!
3 bedrooms, 6 beds, 4 bathrooms
31 Jul – 5 Aug
5.0 out of 5 average rating, 59 reviews
Top guest favourite
Chalet in Killington
Modern and Idyllic Country Getaway Mendon
3 bedrooms, 4 beds, 2.5 bathrooms
14–19 Jul
4.97 out of 5 average rating, 93 reviews