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Search results; Over 1,000 homes in Pittsfield

Guest favourite
Hotel in Pittsfield
Clear River Inn - 2 Double Beds (2nd Floor)
1 bedroom, 2 beds, 1 private bathroom
21–26 Jul
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4.88 out of 5 average rating, 129 reviews
Top guest favourite
Cabin in Pittsfield
Tiny Vermont Cabin!
1 bedroom, 1 queen bed, 1 bathroom
25–30 Jul
4.98 out of 5 average rating, 189 reviews
Bungalow in Pittsfield
Woodland Retreat ~ Green Mtns ~ Hike Bike Ski
2 bedrooms, 4 beds, 1 bathroom
22–27 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Pittsfield
Romantic Retreat, Hot Tub, near Killington Mtn
2 bedrooms, 2 beds, 1 bathroom
8–13 Aug
4.96 out of 5 average rating, 49 reviews
Home in Ludlow
Large Luxury 6br Okemo Home | Hot Tub | Mtn View
6 bedrooms, 12 beds, 4.5 bathrooms
3–8 Aug
New place to stay
Guest favourite
Home in Pittsfield
The Merak Haus – a wooded retreat
3 bedrooms, 8 beds, 2.5 bathrooms
22–27 Jul
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Pittsfield
Skyeburst | Modern Mtn Home
3 bedrooms, 3 beds, 2.5 bathrooms
26–31 Jul
4.98 out of 5 average rating, 40 reviews
Guest favourite
Home in Stockbridge
Ski Home/Arcade Mountain Views Near Killington/Woo
3 bedrooms, 6 beds, 2.5 bathrooms
26–31 Jul
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, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 876 reviews
Top guest favourite
Home in Pittsfield
Killington area Inn all to yourself! 9bd/10 bath
9 bedrooms, 14 beds, 10 bathrooms
23–28 Jul
5.0 out of 5 average rating, 52 reviews
Guest favourite
Home in Pittsfield
VT Cabin, close to Killington Mountain and lakes.
5 bedrooms, 4 beds, 3 bathrooms
26–31 Jul
4.96 out of 5 average rating, 47 reviews
Guest favourite
Home in Killington
NewMont Lodge- Pool, Tennis court, pool table
3 bedrooms, 8 beds, 3 bathrooms
26–31 Jul
4.78 out of 5 average rating, 18 reviews
Top guest favourite
Home in Stockbridge
Unique Mountain Retreat
4 bedrooms, 7 beds, 2 bathrooms
21–26 Jul
5.0 out of 5 average rating, 42 reviews
Guest favourite
Home in Pittsfield
Peak Hill – 3 Bedroom, Hot Tub. Car Charger!
3 bedrooms, 5 beds, 2 bathrooms
26–31 Jul
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Killington
Hot tub|Sauna|Movie Room! 8 min to Killington Mtn!
4 bedrooms, 7 beds, 4 bathrooms
8–13 Aug
5.0 out of 5 average rating, 50 reviews
Top guest favourite
Home in Killington
Private 3 BR/2 BTH w/hot tub, 5 mins to Resort!
3 bedrooms, 6 beds, 2 bathrooms
23–28 Jul
4.96 out of 5 average rating, 84 reviews
Guest favourite
Home in Killington
Beautiful ski house 8 min from mountains
4 bedrooms, 6 queen beds, 2 bathrooms
21–26 Jul
4.88 out of 5 average rating, 93 reviews
Top guest favourite
Chalet in Stockbridge
Gnome Home Mountain Ski Chalet w/Sauna Killington
4 bedrooms, 6 beds, 2 bathrooms
21–26 Jul
4.97 out of 5 average rating, 163 reviews
Top guest favourite
Cabin in Bethel
Phoebe’s Perch
1 bedroom, 3 beds, WC
26–31 Jul
5.0 out of 5 average rating, 16 reviews