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Search results; Over 1,000 homes in Pittsfield

Guest favourite
Serviced apartment in Pittsfield
Clear River Inn - 2 Bedroom Suite
2 bedrooms, 4 beds, 1 private bathroom
16–21 Aug
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4.92 out of 5 average rating, 26 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, 193 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
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
2–7 Sept
4.94 out of 5 average rating, 51 reviews
Top guest favourite
Home in Pittsfield
Skyeburst | Modern Mtn Home
3 bedrooms, 3 beds, 2.5 bathrooms
16–21 Aug
4.98 out of 5 average rating, 43 reviews
Guest favourite
Home in Pittsfield
The Merak Haus – a wooded retreat
3 bedrooms, 8 beds, 2.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Pittsfield
Killington area home - 4 seasons - hot tub and A/C
3 bedrooms, 11 beds, 2.5 bathrooms
16–21 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
17–22 Aug
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Apartment in Killington
On Pico Hike out back door 1 Bedrm 1 night okay
1 bedroom, 3 beds, 1 bathroom
15–20 Aug
4.93 out of 5 average rating, 499 reviews
Guest favourite
Home in Pittsfield
VT Cabin, close to Killington Mountain and lakes.
5 bedrooms, 4 beds, 3 bathrooms
16–21 Aug
4.96 out of 5 average rating, 48 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
Guest favourite
Home in Stockbridge
Ski Home/Arcade Mountain Views Near Killington/Woo
3 bedrooms, 6 beds, 2.5 bathrooms
21–26 Aug
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Home in Killington
Holiday Haus- AC, game room, near golf
3 bedrooms, 6 beds, 2 bathrooms
22–27 Aug
4.97 out of 5 average rating, 37 reviews
Cabin in Bethel
Charming Log Cabin- Private Waterfalls on 9 Acres
3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
New place to stay
Guest favourite
Home in Killington
Cedar Wood Lodge
6 bedrooms, 4 bathrooms
15–20 Aug
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Killington
Post & Beam Home Ideal for Families or Groups
4 bedrooms, 12 beds, 3.5 bathrooms
17–22 Aug
4.95 out of 5 average rating, 38 reviews
Guest favourite
Home in Pittsfield
Peak Hill – 3 Bedroom, Hot Tub. Car Charger!
3 bedrooms, 5 beds, 2 bathrooms
15–20 Aug
5.0 out of 5 average rating, 22 reviews
Guest favourite
Apartment in Killington
3BR at base of Pico Mountain!
3 bedrooms, 7 beds, 2 bathrooms
23–28 Aug
4.93 out of 5 average rating, 122 reviews