filters

Search results; Over 1,000 homes in Pittsfield

Photo 1 of 29
Guest favourite
Home in Pittsfield
Green Mountain/Killington Getaway
3 bedrooms, 6 beds, 2 private bathrooms
1–6 Oct
,
4.84 out of 5 average rating, 88 reviews
Photo 1 of 29
Home in Pittsfield
Green Mountain Farmhouse | 7 Miles to Killington
3 bedrooms, 4 beds, 2.5 bathrooms
19–24 Oct
5.0 out of 5 average rating, 7 reviews
Photo 1 of 29
Top guest favourite
Home in Pittsfield
Skyeburst | Modern Mtn Home
3 bedrooms, 3 beds, 2.5 bathrooms
18–23 Oct
4.98 out of 5 average rating, 46 reviews
Photo 1 of 29
Top guest favourite
Home in Pittsfield
Woodland Acres ~ Green Mtns ~ Hike Bike Ski
2 bedrooms, 4 beds, 1 bathroom
27 Oct – 1 Nov
5.0 out of 5 average rating, 8 reviews
Photo 1 of 29
Top guest favourite
Home in Pittsfield
Trailside Retreat: Hike & Bike From Your Doorstep
3 bedrooms, 6 beds, 2.5 bathrooms
4–9 Oct
4.95 out of 5 average rating, 65 reviews
Photo 1 of 23
Guest favourite
Home in Pittsfield
Romantic Retreat, Hot Tub, near Killington Mtn
2 bedrooms, 2 beds, 1 bathroom
16–21 Oct
4.93 out of 5 average rating, 56 reviews
Photo 1 of 29
Guest favourite
Home in Pittsfield
The Merak Haus – a wooded retreat
3 bedrooms, 8 beds, 2.5 bathrooms
12–17 Oct
5.0 out of 5 average rating, 9 reviews
Photo 1 of 29
Guest favourite
Home in Pittsfield
Killington area home - 4 seasons - hot tub and A/C
3 bedrooms, 11 beds, 2.5 bathrooms
12–17 Oct
4.85 out of 5 average rating, 256 reviews
Photo 1 of 29
Top guest favourite
Holiday home in Pittsfield
The Barn Door Lodge
4 bedrooms, 7 beds, 4.5 bathrooms
1–6 Oct
4.91 out of 5 average rating, 64 reviews
Photo 1 of 29
Guest favourite
Home in Pittsfield
VT Cabin, close to Killington Mountain and lakes.
5 bedrooms, 4 beds, 3 bathrooms
1–6 Oct
4.96 out of 5 average rating, 49 reviews
Photo 1 of 29
Guest favourite
Home in Pittsfield
Killington area entire Inn to yourself! 14bd/15bth
14 bedrooms, 24 beds, 15 bathrooms
4–9 Oct
4.95 out of 5 average rating, 21 reviews
Photo 1 of 29
Top guest favourite
Home in Pittsfield
Killington area Inn all to yourself! 9bd/10 bath
9 bedrooms, 14 beds, 10 bathrooms
18–23 Oct
5.0 out of 5 average rating, 52 reviews
Photo 1 of 29
Guest favourite
Chalet in Pittsfield
Four season Killington/Pico area chalet
3 bedrooms, 6 beds, 1.5 bathrooms
7–12 Dec
4.78 out of 5 average rating, 95 reviews
Photo 1 of 29
Guest favourite
Home in Pittsfield
Peak Hill – 3 Bedroom, Hot Tub. Car Charger!
3 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 23 reviews
Photo 1 of 29
Top guest favourite
Home in Pittsfield
NEW 3BR Home: Hot Tub, AC, EV & Lift Ticket Deals
3 bedrooms, 7 beds, 3 bathrooms
1–6 Oct
5.0 out of 5 average rating, 21 reviews
Photo 1 of 22
Top guest favourite
Home in Stockbridge
Unique Mountain Retreat
4 bedrooms, 7 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 42 reviews
Photo 1 of 29
Guest favourite
Home in Stockbridge
Ski Home/Arcade Mountain Views Near Killington/Woo
3 bedrooms, 6 beds, 2.5 bathrooms
12–18 Oct
5.0 out of 5 average rating, 22 reviews
Photo 1 of 29
Superhost
Hotel in Pittsfield
Clear River Inn - 1 King Bed (2nd Floor)
1 bedroom, 1 king bed, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 7 reviews
Photo 1 of 29
Guest favourite
Home in Pittsfield
A million-dollar view near Killington on 60 acres.
4 bedrooms, 6 beds, 1.5 bathrooms
6–11 May
4.83 out of 5 average rating, 119 reviews