Search results; Over 1,000 homes in Pittsfield

Guest favourite
Home in Pittsfield
Killington area home - 4 seasons - hot tub and A/C
3 bedrooms, 10 beds, 2.5 private bathrooms
17–22 Jul
,
4.85 out of 5 average rating, 254 reviews
Guest favourite
Home in Pittsfield
Post & Beam Vermont Farmhouse | Near Killington
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Jul
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Pittsfield
Romantic Retreat, Hot Tub, near Killington Mtn
2 bedrooms, 2 beds, 1 bathroom
25–30 Jul
4.98 out of 5 average rating, 46 reviews
Bungalow in Pittsfield
Woodland Retreat ~ Bike, Hike, Ski ~ Green Mtns
2 bedrooms, 5 beds, 1 bathroom
1–6 Jul
New place to stay
Guest favourite
Home in Pittsfield
The Merak Haus – a wooded retreat
3 bedrooms, 8 beds, 2.5 bathrooms
7–12 Jul
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Stockbridge
Unique Mountain Retreat
4 bedrooms, 7 beds, 2 bathrooms
7–12 Jul
5.0 out of 5 average rating, 42 reviews
Top guest favourite
Cabin in Leicester
Log Cabin Getaway near Middlebury and Green Mtns
2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
4.98 out of 5 average rating, 871 reviews
Top guest favourite
Home in Pittsfield
Skyeburst | Modern Mtn Home
3 bedrooms, 3 beds, 2.5 bathrooms
6–11 Jul
4.97 out of 5 average rating, 39 reviews
Top guest favourite
Home in Killington
Hot tub|Sauna|Movie Room! 8 min to Killington Mtn!
4 bedrooms, 7 beds, 4 bathrooms
1–6 Jul
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Home in Pittsfield
VT Cabin, close to Killington Mountain and lakes.
5 bedrooms, 4 beds, 3 bathrooms
1–6 Jul
4.98 out of 5 average rating, 46 reviews
Top guest favourite
Holiday home in Pittsfield
The Barn Door Lodge
4 bedrooms, 7 beds, 4.5 bathrooms
1–6 Jul
4.9 out of 5 average rating, 63 reviews
Guest favourite
Home in Killington
Modern Killington A-Frame with Deck & Hot Tub
2 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
4.96 out of 5 average rating, 28 reviews
Top guest favourite
Chalet in Killington
The Overlook - Views | Hot Tub | Fire Pits | Games
3 bedrooms, 5 beds, 2 bathrooms
1–6 Jul
4.97 out of 5 average rating, 103 reviews
Top guest favourite
Cabin in Killington
Killington/ Rutland 2 bedroom Cabin, cabin #4
2 bedrooms, 3 beds, 3 bathrooms
1–6 Jul
5.0 out of 5 average rating, 38 reviews
Guest favourite
Home in Pittsfield
Green Mountain/Killington Getaway
3 bedrooms, 6 beds, 2 bathrooms
10–15 Jul
4.84 out of 5 average rating, 87 reviews
Guest favourite
Home in Pittsfield
Peak Hill – 3 Bedroom, Hot Tub. Car Charger!
3 bedrooms, 5 beds, 2 bathrooms
6–11 Jul
5.0 out of 5 average rating, 20 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, 822 reviews
Guest favourite
Cabin in Bethel
Phoebe’s Perch
1 bedroom, 3 beds, Toilet with sink
5–10 Jul
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Killington
Beautiful ski house 8 min from mountains
4 bedrooms, 6 queen beds, 2 bathrooms
1–6 Jul
4.88 out of 5 average rating, 92 reviews