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Search results; Over 1,000 places in Pittsfield

Guest favourite
Cabin in Pittsfield
Tiny Vermont Cabin!
1 queen bed
3–8 May
4.98 out of 5 average rating, 120 reviews
Guest favourite
Home in Pittsfield
Hideaway Mountain at Killington
5 beds
19–24 Apr
4.97 out of 5 average rating, 37 reviews
Guest favourite
Tiny home in Pittsfield
Tiny Home: VT Mountain Cabin
26 Apr – 1 May
5.0 out of 5 average rating, 16 reviews
Guest favourite
Cabin in Rochester
Black haus: a hip, cool house hidden in a forest.
1 queen bed
29 Jun – 4 Jul
4.95 out of 5 average rating, 390 reviews
Guest favourite
Apartment in Killington
🎿Cozy Fireplace Condo-Mins. to Everything 🚵
2 beds
6–11 May
4.95 out of 5 average rating, 128 reviews
Superhost
Home in Stockbridge
Ski, snow mobile, hiking, fun on slopes & trails!
2 beds
21–26 May
4.76 out of 5 average rating, 58 reviews
Superhost
Chalet in Stockbridge
Vermont Chalet
2 beds
22–27 Apr
4.85 out of 5 average rating, 113 reviews
Guest favourite
Apartment in Pittsfield
Relaxing 1 bedroom Condo in Killington
3 beds
21–26 Apr
5.0 out of 5 average rating, 14 reviews
Guest favourite
Chalet in Stockbridge
Gnome Home Mountain Ski Chalet w/Sauna Killington
6 beds
26 Apr – 1 May
4.95 out of 5 average rating, 84 reviews
Guest favourite
Home in Pittsfield
Beautiful Cabin w/Hot Tub by #1 Golf Course in VT
5 beds
19–24 Apr
4.93 out of 5 average rating, 15 reviews
Guest favourite
Cabin in Rochester
The Langhorne
4 beds
25–30 Apr
5.0 out of 5 average rating, 17 reviews
Home in Pittsfield
South Hill
6 beds
25–30 Apr
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Pittsfield
Mountain Top - Fresh Pond - Killington - Hot Tub
9 beds
22–27 Apr
5.0 out of 5 average rating, 8 reviews
Superhost
Home in Pittsfield
A million-dollar view near Killington on 60 acres.
6 beds
21–26 Apr
4.86 out of 5 average rating, 90 reviews
Superhost
Home in Pittsfield
Killington area home - 4-seasons & hot tub
10 beds
19–24 Apr
4.83 out of 5 average rating, 221 reviews
Guest favourite
Home in Pittsfield
Beautiful Mountain Log Cabin with Scenic Views
7 beds
21–26 Apr
4.91 out of 5 average rating, 149 reviews
Guest favourite
Home in Pittsfield
Curated in Killington -Tweed River House
6 beds
19–24 Apr
5.0 out of 5 average rating, 28 reviews
Guest favourite
Home in Pittsfield
Killington area Inn all to yourself! 9bd/10 bath
14 beds
23–28 Apr
5.0 out of 5 average rating, 30 reviews