Over 1,000 places in Pittsfield

Guest favorite
Cabin in Pittsfield
Tiny Vermont Cabin!
1 queen bed
May 3 – 8
4.98 out of 5 average rating, 120 reviews
Home in Pittsfield
South Hill
6 beds
Apr 26 – May 1
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Stockbridge
Ski, snow mobile, hiking, fun on slopes & trails!
2 beds
May 21 – 26
4.76 out of 5 average rating, 58 reviews
Guest favorite
Home in Pittsfield
Hideaway Mountain at Killington
5 beds
Apr 19 – 24
4.97 out of 5 average rating, 37 reviews
Guest favorite
Chalet in Stockbridge
Gnome Home Mountain Ski Chalet w/Sauna Killington
6 beds
Apr 26 – May 1
4.95 out of 5 average rating, 84 reviews
Guest favorite
Cabin in Rochester
Black haus: a hip, cool house hidden in a forest.
1 queen bed
Jun 29 – Jul 4
4.95 out of 5 average rating, 390 reviews
Guest favorite
Home in Pittsfield
Beautiful Cabin w/Hot Tub by #1 Golf Course in VT
5 beds
Apr 19 – 24
4.93 out of 5 average rating, 15 reviews
Guest favorite
Tiny home in Pittsfield
Tiny Home: VT Mountain Cabin
Apr 26 – May 1
5.0 out of 5 average rating, 16 reviews
Guest favorite
Cabin in Rochester
The Langhorne
4 beds
Apr 26 – May 1
5.0 out of 5 average rating, 17 reviews
Superhost
Chalet in Stockbridge
Vermont Chalet
2 beds
Apr 22 – 27
4.85 out of 5 average rating, 113 reviews
Superhost
Home in Pittsfield
A million-dollar view near Killington on 60 acres.
6 beds
Apr 22 – 27
4.86 out of 5 average rating, 90 reviews
Guest favorite
Condo in Pittsfield
Relaxing 1 bedroom Condo in Killington
3 beds
Apr 21 – 26
5.0 out of 5 average rating, 14 reviews
Superhost
Home in Pittsfield
Killington area home - 4-seasons & hot tub
10 beds
Apr 19 – 24
4.83 out of 5 average rating, 221 reviews
Guest favorite
Home in Pittsfield
Beautiful Mountain Log Cabin with Scenic Views
7 beds
Apr 22 – 27
4.91 out of 5 average rating, 149 reviews
Superhost
Home in Pittsfield
Mountain Top - Fresh Pond - Killington - Hot Tub
9 beds
Apr 22 – 27
5.0 out of 5 average rating, 8 reviews
Guest favorite
Home in Pittsfield
Curated in Killington -Tweed River House
6 beds
Apr 20 – 25
5.0 out of 5 average rating, 28 reviews
Guest favorite
Home in Pittsfield
Killington area Inn all to yourself! 9bd/10 bath
14 beds
Apr 23 – 28
5.0 out of 5 average rating, 30 reviews
Guest favorite
Home in Rochester
Secluded Oasis: Sugarbush, Killington, Mtn Biking
4 beds
Apr 22 – 27
5.0 out of 5 average rating, 42 reviews