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Search results; Over 1,000 homes in Pittsfield

Guest favourite
Home in Pittsfield
Green Mountain/Killington Getaway
3 bedrooms, 6 beds, 2 private bathrooms
4–9 Aug
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4.84 out of 5 average rating, 88 reviews
Guest favourite
Home in Pittsfield
Romantic Retreat, Hot Tub, near Killington Mtn
2 bedrooms, 2 beds
8–13 Aug
4.94 out of 5 average rating, 50 reviews
Top guest favourite
Cabin in Pittsfield
Tiny Vermont Cabin!
1 bedroom, 1 queen bed
9–14 Aug
4.98 out of 5 average rating, 191 reviews
Bungalow in Pittsfield
Woodland Retreat ~ Green Mtns ~ Hike Bike Ski
2 bedrooms, 4 beds
22–27 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Pittsfield
Peak Hill – 3 Bedroom, Hot Tub. Car Charger!
3 bedrooms, 5 beds
6–11 Aug
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Pittsfield
Skyeburst | Modern Mtn Home
3 bedrooms, 3 beds
4–9 Aug
4.98 out of 5 average rating, 42 reviews
Guest favourite
Home in Pittsfield
The Merak Haus – a wooded retreat
3 bedrooms, 8 beds
11–16 Aug
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Killington
Holiday Haus- AC, game room, near golf
3 bedrooms, 6 beds
11–16 Aug
4.97 out of 5 average rating, 35 reviews
Top guest favourite
Home in Stockbridge
Unique Mountain Retreat
4 bedrooms, 7 beds
4–9 Aug
5.0 out of 5 average rating, 42 reviews
Top guest favourite
Home in Killington
Cedar Wood Lodge
6 bedrooms
9–14 Aug
5.0 out of 5 average rating, 16 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 Killington
|Hot tub|Sauna | 3k sqft|100 inch TV|Massage Chair
5 bedrooms, 8 beds
23–28 Aug
5.0 out of 5 average rating, 19 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
Home in Pittsfield
Killington area Inn all to yourself! 9bd/10 bath
9 bedrooms, 14 beds
4–9 Aug
5.0 out of 5 average rating, 52 reviews
Guest favourite
Home in Pittsfield
Killington area home - 4 seasons - hot tub and A/C
3 bedrooms, 10 beds
16–21 Aug
4.85 out of 5 average rating, 256 reviews
Guest favourite
Home in Pittsfield
Riverside Retreat: Hike & Bike From Your Doorstep
3 bedrooms, 6 beds
9–14 Aug
4.95 out of 5 average rating, 63 reviews
Top guest favourite
Chalet in Stockbridge
Gnome Home Mountain Ski Chalet w/Sauna Killington
4 bedrooms, 6 beds
4–9 Aug
4.97 out of 5 average rating, 164 reviews
Guest favourite
Home in Killington
Killington Chalet: Hot Tub, Fireplace, spacious 4b
4 bedrooms, 5 beds
30 Aug – 4 Sept
4.94 out of 5 average rating, 68 reviews
Superhost
Home in Killington
Ski with Fireplace • EV Charger • Minutes to
4 bedrooms, 5 beds
5–10 Aug