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Search results; Over 1,000 homes in Pittsfield

Top guest favourite
Home in Pittsfield
VT Cabin, close to Killington Mountain and lakes.
5 bedrooms, 4 beds, 3 private bathrooms
9–14 Jul
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4.98 out of 5 average rating, 46 reviews
Guest favourite
Home in Pittsfield
Post & Beam Vermont Farmhouse | Near Killington
3 bedrooms, 4 beds, 2.5 bathrooms
11–16 Jul
5.0 out of 5 average rating, 6 reviews
Bungalow in Pittsfield
Woodland Retreat ~ Green Mtns ~ Hike Bike Ski
2 bedrooms, 4 beds, 1 bathroom
12–17 Jul
New place to stay
Guest favourite
Home in Pittsfield
Green Mountain/Killington Getaway
3 bedrooms, 6 beds, 2 bathrooms
12–17 Jul
4.84 out of 5 average rating, 87 reviews
Top guest favourite
Home in Pittsfield
Skyeburst | Modern Mtn Home
3 bedrooms, 3 beds, 2.5 bathrooms
10–15 Jul
4.98 out of 5 average rating, 40 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
Home in Pittsfield
Peak Hill – 3 Bedroom, Hot Tub. Car Charger!
3 bedrooms, 5 beds, 2 bathrooms
9–14 Jul
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Home in Killington
Cedar Wood Lodge
6 bedrooms, 4 bathrooms
9–14 Jul
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Killington
Hot tub|Sauna|Movie Room! 8 min to Killington Mtn!
4 bedrooms, 7 beds, 4 bathrooms
22–27 Jul
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Cabin in Leicester
Log Cabin Getaway near Middlebury and Green Mtns
2 bedrooms, 3 beds, 1 bathroom
11–16 Aug
4.98 out of 5 average rating, 872 reviews
Guest favourite
Cabin in Goshen
The Berghüttli: Glowing Swiss Hut in the Forest
2 bedrooms, 2 beds, 1 bathroom
19–24 Jul
4.97 out of 5 average rating, 141 reviews
Guest favourite
Chalet in Stockbridge
Vermont Chalet
2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
4.86 out of 5 average rating, 196 reviews
Guest favourite
Home in Killington
Beautiful ski house 8 min from mountains
4 bedrooms, 6 queen beds, 2 bathrooms
9–14 Jul
4.88 out of 5 average rating, 93 reviews
Top guest favourite
Home in Pittsfield
Killington area Inn all to yourself! 9bd/10 bath
9 bedrooms, 14 beds, 10 bathrooms
9–14 Jul
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Flat in Killington
Jack S'Bearo- AC, Pool, Mountain Views, Hiking Gym
1 bedroom, 2 beds, 1 bathroom
9–14 Jul
4.98 out of 5 average rating, 115 reviews
Guest favourite
Home in Killington
Killington Chalet: Hot Tub, Fireplace, spacious 4b
4 bedrooms, 5 beds, 2 bathrooms
16–21 Aug
4.94 out of 5 average rating, 65 reviews
Top guest favourite
Flat in Killington
Private Killington Retreat | Hot Tub | Fireplace
2 bedrooms, 3 beds, 1 bathroom
18–23 Jul
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Room in Mendon
Private fireplace suite & luxury bath - Killington
1 queen bed, 1 bathroom
19–24 Jul
4.99 out of 5 average rating, 825 reviews
Top guest favourite
Cabin in Killington
Killington/ Rutland 2 bedroom Cabin, cabin #4
2 bedrooms, 3 beds, 3 bathrooms
9–14 Jul
4.97 out of 5 average rating, 39 reviews