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Search results; Over 1,000 homes in Pittsfield

Chalet in Pittsfield
Luxury Heart of VT Green Mountains
3 bedrooms, 4 beds, 3.5 private bathrooms
10–15 Jul
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4.95 out of 5 average rating, 57 reviews
Top guest favourite
Home in Pittsfield
Skyeburst | Modern Mtn Home
4.98 out of 5 average rating, 40 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
10–15 Jul
Guest favourite
Home in Pittsfield
Post & Beam Vermont Farmhouse | Near Killington
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
7–12 Sept
Bungalow in Pittsfield
Woodland Retreat ~ Green Mtns ~ Hike Bike Ski
New place to stay, 2 bedrooms, 4 beds, 1 bathroom
29 Jul – 3 Aug
Guest favourite
Home in Pittsfield
Romantic Retreat, Hot Tub, near Killington Mtn
4.96 out of 5 average rating, 48 reviews, 2 bedrooms, 2 beds, 1 bathroom
25–30 Jul
Top guest favourite
Home in Pittsfield
VT Cabin, close to Killington Mountain and lakes.
4.96 out of 5 average rating, 47 reviews, 5 bedrooms, 4 beds, 3 bathrooms
10–15 Jul
Guest favourite
Home in Pittsfield
Peak Hill – 3 Bedroom, Hot Tub. Car Charger!
5.0 out of 5 average rating, 20 reviews, 3 bedrooms, 5 beds, 2 bathrooms
10–15 Jul
Top guest favourite
Cabin in Pittsfield
Tiny Vermont Cabin!
4.98 out of 5 average rating, 188 reviews, 1 bedroom, 1 bed, 1 bathroom
13–18 Jul
Top guest favourite
Home in Pittsfield
The Fiddlehead Lodge (Green Mountain Getaway)
5.0 out of 5 average rating, 13 reviews, 4 bedrooms, 9 beds, 1.5 bathrooms
10–15 Jul
Top guest favourite
Home in Killington
Hot tub|Sauna|Movie Room! 8 min to Killington Mtn!
5.0 out of 5 average rating, 49 reviews, 4 bedrooms, 7 beds, 4 bathrooms
26–31 Jul
Guest favourite
Home in Pittsfield
Green Mountain/Killington Getaway
4.84 out of 5 average rating, 87 reviews, 3 bedrooms, 6 beds, 2 bathrooms
12–17 Jul
Top guest favourite
Home in Pittsfield
Killington area entire Inn to yourself! 14bd/15bth
5.0 out of 5 average rating, 18 reviews, 14 bedrooms, 24 beds, 15 bathrooms
19–24 Jul
Top guest favourite
Home in Pittsfield
Killington area Inn all to yourself! 9bd/10 bath
5.0 out of 5 average rating, 52 reviews, 9 bedrooms, 14 beds, 10 bathrooms
10–15 Jul
Guest favourite
Home in Pittsfield
The Merak Haus – a wooded retreat
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 8 beds, 2.5 bathrooms
12–17 Jul
Guest favourite
Home in Pittsfield
Trailside Retreat: Hike & Bike From Your Doorstep
4.95 out of 5 average rating, 63 reviews, 3 bedrooms, 6 beds, 2.5 bathrooms
17–22 Jul
Guest favourite
Home in Pittsfield
Killington area home - 4 seasons - hot tub and A/C
4.85 out of 5 average rating, 255 reviews, 3 bedrooms, 10 beds, 2.5 bathrooms
16–21 Aug
Guest favourite
Home in Stockbridge
Ski/MTB/Arcade/Pool Table near Killington/Pico/Sug
5.0 out of 5 average rating, 10 reviews, 6 bedrooms, 10 beds, 5 bathrooms
26–31 Jul
Guest favourite
Hotel in Pittsfield
Clear River Inn - 2 Double Beds (2nd Floor)
4.88 out of 5 average rating, 129 reviews, 1 bedroom, 2 beds, 1 bathroom
10–15 Jul
Top guest favourite
Home in Stockbridge
Riverfront Retreat in Stockbridge
5.0 out of 5 average rating, 28 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
2–7 Aug