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Search results; Over 1,000 homes in Pittsfield

Top guest favourite
Home in Pittsfield
VT Cabin, close to Killington Mountain and lakes.
5 bedrooms, 4 beds, 3 private bathrooms
9–14 Jul
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4.98 out of 5 average rating, 46 reviews
Guest favourite
Home in Pittsfield
Post & Beam Vermont Farmhouse | Near Killington
3 bedrooms, 4 beds, 2.5 bathrooms
11–16 Jul
5.0 out of 5 average rating, 6 reviews
Bungalow in Pittsfield
Woodland Retreat ~ Green Mtns ~ Hike Bike Ski
2 bedrooms, 4 beds, 1 bathroom
12–17 Jul
New place to stay
Top guest favourite
Cabin in Pittsfield
Tiny Vermont Cabin!
1 bedroom, 1 queen bed, 1 bathroom
13–18 Jul
4.98 out of 5 average rating, 188 reviews
Guest favourite
Home in Pittsfield
Green Mountain/Killington Getaway
3 bedrooms, 6 beds, 2 bathrooms
12–17 Jul
4.84 out of 5 average rating, 87 reviews
Top guest favourite
Home in Pittsfield
Skyeburst | Modern Mtn Home
3 bedrooms, 3 beds, 2.5 bathrooms
9–14 Jul
4.98 out of 5 average rating, 40 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
Top guest favourite
Home in Killington
Hot tub|Sauna|Movie Room! 8 min to Killington Mtn!
4 bedrooms, 7 beds, 4 bathrooms
26–31 Jul
5.0 out of 5 average rating, 49 reviews
Guest favourite
Home in Pittsfield
Peak Hill – 3 Bedroom, Hot Tub. Car Charger!
3 bedrooms, 5 beds, 2 bathrooms
9–14 Jul
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Cabin in Leicester
Log Cabin Getaway near Middlebury and Green Mtns
2 bedrooms, 3 beds, 1 bathroom
11–16 Aug
4.98 out of 5 average rating, 872 reviews
Guest favourite
Home in Killington
Killington Chalet: Hot Tub, Fireplace, spacious 4b
4 bedrooms, 5 beds, 2 bathrooms
16–21 Aug
4.94 out of 5 average rating, 65 reviews
Top guest favourite
Home in Killington
Cedar Wood Lodge
6 bedrooms, 4 bathrooms
9–14 Jul
5.0 out of 5 average rating, 16 reviews
Guest favourite
Cabin in Goshen
The Berghüttli: Glowing Swiss Hut in the Forest
2 bedrooms, 2 beds, 1 bathroom
19–24 Jul
4.97 out of 5 average rating, 141 reviews
Guest favourite
Home in Killington
Beautiful ski house 8 min from mountains
4 bedrooms, 6 queen beds, 2 bathrooms
19–24 Jul
4.88 out of 5 average rating, 93 reviews
Guest favourite
Home in Killington
Fun In Fun Out Up: 3BR, 2BA. Hot Tub. Sauna.
3 bedrooms, 5 beds, 2 bathrooms
19–24 Jul
4.97 out of 5 average rating, 29 reviews
Top guest favourite
Home in Killington
|Hot tub|Sauna | 3k sqft|100 inch TV|Massage Chair
5 bedrooms, 8 beds, 4.5 bathrooms
9–14 Jul
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Pittsfield
The Merak Haus – a wooded retreat
3 bedrooms, 8 beds, 2.5 bathrooms
11–16 Jul
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Stockbridge
Ski Home/Arcade Mountain Views Near Killington/Woo
3 bedrooms, 6 beds, 2.5 bathrooms
9–14 Jul
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Pittsfield
The Fiddlehead Lodge (Green Mountain Getaway)
4 bedrooms, 9 beds, 1.5 bathrooms
9–14 Jul
5.0 out of 5 average rating, 13 reviews