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Search results; Over 1,000 homes in Pittsfield

Guest favourite
Home in Pittsfield
A million-dollar view near Killington on 60 acres.
4 bedrooms, 6 beds, 1.5 private bathrooms
6–11 May
,
4.83 out of 5 average rating, 119 reviews
Guest favourite
Cabin in Pittsfield
Tiny Vermont Cabin!
1 bedroom, 1 queen bed
30 Aug – 4 Sept
4.98 out of 5 average rating, 193 reviews
Guest favourite
Bungalow in Pittsfield
Woodland Acres ~ Green Mtns ~ Hike Bike Ski
2 bedrooms, 4 beds
21–26 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Pittsfield
Romantic Retreat, Hot Tub, near Killington Mtn
2 bedrooms, 2 beds
2–7 Sept
4.94 out of 5 average rating, 52 reviews
Guest favourite
Home in Pittsfield
Post & Beam Vermont Farmhouse | Near Killington
3 bedrooms, 4 beds
4–9 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Pittsfield
Skyeburst | Modern Mtn Home
3 bedrooms, 3 beds
16–21 Aug
4.98 out of 5 average rating, 43 reviews
Guest favourite
Home in Pittsfield
Killington area home - 4 seasons - hot tub and A/C
3 bedrooms, 11 beds
16–21 Aug
4.85 out of 5 average rating, 256 reviews
Top guest favourite
Home in Pittsfield
Killington area Inn all to yourself! 9bd/10 bath
9 bedrooms, 14 beds
17–22 Aug
5.0 out of 5 average rating, 52 reviews
Superhost
Home in Killington
Ski, Bike, Hike. Golf. - AC - Killington.
3 bedrooms, 4 beds
30 Aug – 4 Sept
Guest favourite
Home in Pittsfield
Green Mountain/Killington Getaway
3 bedrooms, 6 beds
16–21 Aug
4.84 out of 5 average rating, 88 reviews
Top guest favourite
Home in Pittsfield
NEW 3BR Home: Hot Tub, AC, EV & Lift Ticket Deals
3 bedrooms, 7 beds
17–22 Aug
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Pittsfield
The Merak Haus – a wooded retreat
3 bedrooms, 8 beds
18–23 Aug
5.0 out of 5 average rating, 9 reviews
Cabin in Bethel
Charming Log Cabin- Private Waterfalls on 9 Acres
3 bedrooms, 4 beds
28 Sept – 3 Oct
New place to stay
Top guest favourite
Cabin in Goshen
The Berghüttli: Glowing Swiss Hut in the Forest
2 bedrooms, 2 beds
20–25 Sept
4.97 out of 5 average rating, 146 reviews
Guest favourite
Home in Stockbridge
Ski Home/Arcade Mountain Views Near Killington/Woo
3 bedrooms, 6 beds
21–26 Aug
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Cabin in Leicester
Log Cabin Getaway near Middlebury and Green Mtns
2 bedrooms, 3 beds
13–18 Sept
4.98 out of 5 average rating, 879 reviews
Guest favourite
Home in Pittsfield
Peak Hill – 3 Bedroom, Hot Tub. Car Charger!
3 bedrooms, 5 beds
16–21 Aug
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Home in Killington
Holiday Haus- AC, game room, near golf
3 bedrooms, 6 beds
22–27 Aug
4.97 out of 5 average rating, 37 reviews
Guest favourite
Home in Killington
Entire home- Killington, Vermont Ski, Hike, Bike
3 bedrooms, 4 beds
17–22 Aug
5.0 out of 5 average rating, 19 reviews