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Search results; Over 1,000 homes in Pittsfield

Guest favourite
Hotel in Pittsfield
Clear River Inn - 2 Double Beds (2nd Floor)
1 bedroom, 2 beds, 1 private bathroom
13–18 Aug
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4.88 out of 5 average rating, 129 reviews
Guest favourite
Cabin in Pittsfield
Tiny Vermont Cabin!
1 bedroom, 1 queen bed
30 Aug – 4 Sept
4.98 out of 5 average rating, 193 reviews
Top guest favourite
Bungalow in Pittsfield
Woodland Retreat ~ Green Mtns ~ Hike Bike Ski
2 bedrooms, 4 beds
21–26 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Pittsfield
Romantic Retreat, Hot Tub, near Killington Mtn
2 bedrooms, 2 beds
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
16–21 Aug
4.98 out of 5 average rating, 43 reviews
Guest favourite
Home in Pittsfield
Post & Beam Vermont Farmhouse | Near Killington
3 bedrooms, 4 beds
4–9 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Pittsfield
Peak Hill – 3 Bedroom, Hot Tub. Car Charger!
3 bedrooms, 5 beds
13–18 Aug
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Home in Pittsfield
Killington area Inn all to yourself! 9bd/10 bath
9 bedrooms, 14 beds
17–22 Aug
5.0 out of 5 average rating, 52 reviews
Guest favourite
Home in Pittsfield
Killington area home - 4 seasons - hot tub and A/C
3 bedrooms, 11 beds
16–21 Aug
4.85 out of 5 average rating, 256 reviews
Guest favourite
Home in Stockbridge
Ski Home/Arcade Mountain Views Near Killington/Woo
3 bedrooms, 6 beds
21–26 Aug
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Home in Pittsfield
NEW 3BR Home: Hot Tub, AC, EV & Lift Ticket Deals
3 bedrooms, 4 beds
17–22 Aug
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Pittsfield
VT Cabin, close to Killington Mountain and lakes.
5 bedrooms, 4 beds
16–21 Aug
4.96 out of 5 average rating, 48 reviews
Top guest favourite
Cabin in Goshen
The Berghüttli: Glowing Swiss Hut in the Forest
2 bedrooms, 2 beds
20–25 Sept
4.97 out of 5 average rating, 146 reviews
Cabin in Bethel
Charming Log Cabin- Private Waterfalls on 9 Acres
3 bedrooms, 4 beds
28 Sept – 3 Oct
New place to stay
Top guest favourite
Apartment in Killington
On Pico Hike out back door 1 Bedrm 1 night okay
1 bedroom, 3 beds
13–18 Aug
4.93 out of 5 average rating, 499 reviews
Guest favourite
Home in Pittsfield
The Merak Haus – a wooded retreat
3 bedrooms, 8 beds
15–20 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Apartment in Killington
3BR at base of Pico Mountain!
3 bedrooms, 7 beds
16–21 Aug
4.93 out of 5 average rating, 122 reviews
Guest favourite
Home in Killington
Killington Mountain Farmhouse-5 min to Skiing
4 bedrooms, 8 beds
17–22 Aug
4.87 out of 5 average rating, 23 reviews
Top guest favourite
Home in Stockbridge
Riverfront Retreat in Stockbridge
3 bedrooms, 4 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 35 reviews