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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
13–18 Jul
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4.98 out of 5 average rating, 188 reviews
Bungalow in Pittsfield
Woodland Retreat ~ Green Mtns ~ Hike Bike Ski
New place to stay, 2 bedrooms, 4 beds, 1 bathroom
12–17 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
Skyeburst | Modern Mtn Home
4.98 out of 5 average rating, 40 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
10–15 Jul
Guest favourite
Home in Pittsfield
Romantic Retreat, Hot Tub, near Killington Mtn
4.96 out of 5 average rating, 48 reviews, 2 bedrooms, 2 beds, 1 bathroom
25–30 Jul
Top guest favourite
Home in Killington
Hot tub|Sauna|Movie Room! 8 min to Killington Mtn!
5.0 out of 5 average rating, 49 reviews, 4 bedrooms, 7 beds, 4 bathrooms
26–31 Jul
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
10–15 Jul
Top 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
10–15 Jul
Top guest favourite
Cabin in Leicester
Log Cabin Getaway near Middlebury and Green Mtns
4.98 out of 5 average rating, 872 reviews, 2 bedrooms, 3 beds, 1 bathroom
11–16 Aug
Guest favourite
Cabin in Goshen
The Berghüttli: Glowing Swiss Hut in the Forest
4.97 out of 5 average rating, 141 reviews, 2 bedrooms, 2 beds, 1 bathroom
19–24 Jul
Top guest favourite
Home in Killington
|Hot tub|Sauna | 3k sqft|100 inch TV|Massage Chair
5.0 out of 5 average rating, 18 reviews, 5 bedrooms, 8 beds, 4.5 bathrooms
10–15 Jul
Top guest favourite
Flat in Killington
Private Killington Retreat | Hot Tub | Fireplace
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 3 beds, 1 bathroom
18–23 Jul
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
10–15 Jul
Guest favourite
Home in Killington
Beautiful ski house 8 min from mountains
4.88 out of 5 average rating, 93 reviews, 4 bedrooms, 6 beds, 2 bathrooms
19–24 Jul
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
12–17 Jul
Guest favourite
Home in Pittsfield
Green Mountain/Killington Getaway
4.84 out of 5 average rating, 87 reviews, 3 bedrooms, 6 beds, 2 bathrooms
12–17 Jul
Top guest favourite
Home in Pittsfield
The Fiddlehead Lodge (Green Mountain Getaway)
5.0 out of 5 average rating, 13 reviews, 4 bedrooms, 9 beds, 1.5 bathrooms
10–15 Jul
Top guest favourite
Home in Killington
Hot Tub|Sauna|Relax! 5 mins to downtown Killington
4.98 out of 5 average rating, 48 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
19–24 Jul
Top guest favourite
Home in Stockbridge
Ski Home/Arcade Mountain Views Near Killington/Woo
5.0 out of 5 average rating, 21 reviews, 3 bedrooms, 6 beds, 2.5 bathrooms
12–17 Jul