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Search results; Over 1,000 homes in Pittsfield

Top guest favourite
Holiday home in Pittsfield
The Barn Door Lodge
4 bedrooms, 7 beds, 4.5 private bathrooms
20–25 Aug
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4.91 out of 5 average rating, 64 reviews
Guest favourite
Cabin in Pittsfield
Tiny Vermont Cabin!
1 bedroom, 1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 194 reviews
Home in Pittsfield
Post & Beam Vermont Farmhouse | Near Killington
3 bedrooms, 4 beds, 2.5 bathrooms
4–9 Sept
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
1–6 Sept
4.94 out of 5 average rating, 52 reviews
Guest favourite
Bungalow in Pittsfield
Woodland Acres ~ Green Mtns ~ Hike Bike Ski
2 bedrooms, 4 beds, 1 bathroom
21–26 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Pittsfield
Killington area home - 4 seasons - hot tub and A/C
3 bedrooms, 11 beds, 2.5 bathrooms
20–25 Aug
4.85 out of 5 average rating, 256 reviews
Top guest favourite
Home in Pittsfield
Killington area Inn all to yourself! 9bd/10 bath
9 bedrooms, 14 beds, 10 bathrooms
20–25 Aug
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Home in Pittsfield
Skyeburst | Modern Mtn Home
3 bedrooms, 3 beds, 2.5 bathrooms
24–29 Aug
4.98 out of 5 average rating, 43 reviews
Top guest favourite
Home in Pittsfield
NEW 3BR Home: Hot Tub, AC, EV & Lift Ticket Deals
3 bedrooms, 7 beds, 3 bathrooms
20–25 Aug
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Pittsfield
Peak Hill – 3 Bedroom, Hot Tub. Car Charger!
3 bedrooms, 5 beds, 2 bathrooms
20–25 Aug
5.0 out of 5 average rating, 23 reviews
Guest favourite
Home in Pittsfield
The Merak Haus – a wooded retreat
3 bedrooms, 8 beds, 2.5 bathrooms
21–26 Aug
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Killington
Hot Tub|Sauna|Relax! 5 mins to downtown Killington
3 bedrooms, 3 beds, 2.5 bathrooms
30 Aug – 4 Sept
4.98 out of 5 average rating, 53 reviews
Top guest favourite
Chalet in Stockbridge
Gnome Home Mountain Ski Chalet w/Sauna Killington
4 bedrooms, 6 beds, 2 bathrooms
27 Aug – 1 Sept
4.97 out of 5 average rating, 164 reviews
Top guest favourite
Cabin in Leicester
Log Cabin Getaway near Middlebury and Green Mtns
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 879 reviews
Top guest favourite
Home in Killington
The Big Lebearski- AC, Grill, Fire Pit, Hot tub!
4 bedrooms, 5 beds, 2.5 bathrooms
23–28 Aug
4.99 out of 5 average rating, 173 reviews
Top guest favourite
Apartment in Killington
On Pico Hike out back door 1 Bedrm 1 night okay
1 bedroom, 3 beds, 1 bathroom
22–27 Aug
4.93 out of 5 average rating, 499 reviews
Guest favourite
Home in Pittsfield
Trailside Retreat: Hike & Bike From Your Doorstep
3 bedrooms, 6 beds, 2.5 bathrooms
24–29 Aug
4.95 out of 5 average rating, 64 reviews
Guest favourite
Home in Killington
Killington Chalet: Hot Tub, Fireplace, spacious 4b
4 bedrooms, 5 beds, 2 bathrooms
12–17 Sept
4.94 out of 5 average rating, 71 reviews
Guest favourite
Home in Killington
Entire home- Killington, Vermont Ski, Hike, Bike
3 bedrooms, 4 beds, 2.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 19 reviews