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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
30 Aug – 4 Sept
,
4.98 out of 5 average rating, 193 reviews
Bungalow in Pittsfield
Woodland Retreat ~ Green Mtns ~ Hike Bike Ski
2 bedrooms, 4 beds, 1 bathroom
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, 1 bathroom
19–24 Aug
4.94 out of 5 average rating, 51 reviews
Guest favourite
Home in Pittsfield
Post & Beam Vermont Farmhouse | Near Killington
3 bedrooms, 4 beds, 2.5 bathrooms
4–9 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Pittsfield
Killington area Inn all to yourself! 9bd/10 bath
9 bedrooms, 14 beds, 10 bathrooms
17–22 Aug
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Home in Pittsfield
Skyeburst | Modern Mtn Home
3 bedrooms, 3 beds, 2.5 bathrooms
16–21 Aug
4.98 out of 5 average rating, 43 reviews
Guest favourite
Home in Pittsfield
Peak Hill – 3 Bedroom, Hot Tub. Car Charger!
3 bedrooms, 5 beds, 2 bathrooms
11–16 Aug
5.0 out of 5 average rating, 22 reviews
Guest favourite
Home in Pittsfield
VT Cabin, close to Killington Mountain and lakes.
5 bedrooms, 4 beds, 3 bathrooms
16–21 Aug
4.96 out of 5 average rating, 48 reviews
Guest favourite
Home in Pittsfield
Killington area home - 4 seasons - hot tub and A/C
3 bedrooms, 11 beds, 2.5 bathrooms
16–21 Aug
4.85 out of 5 average rating, 256 reviews
Guest favourite
Home in Stockbridge
Ski Home/Arcade Mountain Views Near Killington/Woo
3 bedrooms, 6 beds, 2.5 bathrooms
21–26 Aug
5.0 out of 5 average rating, 22 reviews
Guest favourite
Home in Pittsfield
The Merak Haus – a wooded retreat
3 bedrooms, 8 beds, 2.5 bathrooms
13–18 Aug
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Pittsfield
NEW 3BR Home: Hot Tub, AC, EV & Lift Ticket Deals
3 bedrooms, 4 beds, 3 bathrooms
17–22 Aug
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Cabin in Leicester
Log Cabin Getaway near Middlebury and Green Mtns
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 879 reviews
Top guest favourite
Home in Killington
|Hot tub|Sauna | 3k sqft|100 inch TV|Massage Chair
5 bedrooms, 8 beds, 4.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Home in Pittsfield
The Fiddlehead Lodge (Green Mountain Getaway)
4 bedrooms, 9 beds, 1.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 14 reviews
Guest favourite
Home in Pittsfield
Riverside Retreat: Hike & Bike From Your Doorstep
3 bedrooms, 6 beds, 2.5 bathrooms
21–26 Aug
4.95 out of 5 average rating, 63 reviews
Guest favourite
Home in Killington
Killington Mountain Farmhouse-5 min to Skiing
4 bedrooms, 8 beds, 3 bathrooms
17–22 Aug
4.87 out of 5 average rating, 23 reviews
Guest favourite
Apartment in Killington
3BR at base of Pico Mountain!
3 bedrooms, 7 beds, 2 bathrooms
16–21 Aug
4.93 out of 5 average rating, 122 reviews
Top guest favourite
Home in Stockbridge
Riverfront Retreat in Stockbridge
3 bedrooms, 4 beds, 1.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 34 reviews