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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
13–18 Jul
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4.98 out of 5 average rating, 188 reviews
Guest favourite
Home in Pittsfield
Romantic Retreat, Hot Tub, near Killington Mtn
2 bedrooms, 2 beds, 1 bathroom
25–30 Jul
4.96 out of 5 average rating, 48 reviews
Guest favourite
Hotel in Pittsfield
Clear River Inn - 1 King Bed (Ground Floor)
1 bedroom, 1 king bed, 1 bathroom
14–19 Jul
4.76 out of 5 average rating, 25 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
Top guest favourite
Home in Pittsfield
Killington area entire Inn to yourself! 14bd/15bth
14 bedrooms, 24 beds, 15 bathrooms
19–24 Jul
5.0 out of 5 average rating, 18 reviews
Bungalow in Pittsfield
Woodland Retreat ~ Green Mtns ~ Hike Bike Ski
2 bedrooms, 4 beds, 1 bathroom
29 Jul – 3 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Pittsfield
Skyeburst | Modern Mtn Home
3 bedrooms, 3 beds, 2.5 bathrooms
19–24 Jul
4.98 out of 5 average rating, 40 reviews
Guest favourite
Home in Pittsfield
Peak Hill – 3 Bedroom, Hot Tub. Car Charger!
3 bedrooms, 5 beds, 2 bathrooms
12–17 Jul
5.0 out of 5 average rating, 20 reviews
Top 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, 21 reviews
Top guest favourite
Holiday home in Pittsfield
The Barn Door Lodge
4 bedrooms, 7 beds, 4.5 bathrooms
12–17 Jul
4.9 out of 5 average rating, 63 reviews
Top guest favourite
Apartment in Killington
CozyCub- Pool, AC, Hiking, Mountain Biking, Tennis
1 bedroom, 2 beds, 1 bathroom
9–14 Aug
4.93 out of 5 average rating, 230 reviews
Top guest favourite
Flat in Killington
Jack S'Bearo- AC, Pool, Mountain Views, Hiking Gym
1 bedroom, 2 beds, 1 bathroom
19–24 Jul
4.98 out of 5 average rating, 116 reviews
Guest favourite
Home in Pittsfield
Post & Beam Vermont Farmhouse | Near Killington
3 bedrooms, 4 beds, 2.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Stockbridge
Unique Mountain Retreat
4 bedrooms, 7 beds, 2 bathrooms
12–17 Jul
5.0 out of 5 average rating, 42 reviews
Top guest favourite
Home in Killington
Hot Tub|Sauna|Relax! 5 mins to downtown Killington
3 bedrooms, 3 beds, 2.5 bathrooms
19–24 Jul
4.98 out of 5 average rating, 49 reviews
Top guest favourite
Chalet in Stockbridge
Gnome Home Mountain Ski Chalet w/Sauna Killington
4 bedrooms, 6 beds, 2 bathrooms
20–26 Jul
4.97 out of 5 average rating, 163 reviews
Guest favourite
Home in Pittsfield
The Merak Haus – a wooded retreat
3 bedrooms, 8 beds, 2.5 bathrooms
14–19 Jul
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Pittsfield
The Guernsey Brook Cabin
3 bedrooms, 5 beds, 2 bathrooms
12–17 Jul
5.0 out of 5 average rating, 14 reviews
Superhost
Flat in Killington
Bernie’s Bear Den- pool, hot tub, private sauna
2 bedrooms, 5 beds, 2.5 bathrooms
12–17 Jul