House holiday rentals in Pittsfield
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Top-rated house rentals in Pittsfield
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for house rentals in Pittsfield
House rentals with a pool
Home in Killington
4.92 out of 5 average rating, 165 reviewsCozy Condo Tucked in the Heart of Killington
28 Aug – 4 Sep
Home in Plainfield
4.89 out of 5 average rating, 119 reviewsHistoric Home on 17 acres of land. Go escape!
27 Dec – 3 Jan
Home in Warren
4.81 out of 5 average rating, 107 reviewsCharming Sugarbush Standalone Condo
3–10 May
Home in Killington
5.0 out of 5 average rating, 31 reviewsBearmont! Pool, HotTub, AC, FirePit
1–8 Jun
Home in Killington
5.0 out of 5 average rating, 28 reviews* Slope Side Sauna w/ Shuttle *
11–18 Jul
Home in Chittenden
4.9 out of 5 average rating, 81 reviewsComfortable, relaxing large country home
23–30 Sep
Home in Killington
4.97 out of 5 average rating, 37 reviews2 Minute Shuttle to the Slopes Unit 9
11–18 Mar
Home in Bridgewater
4.9 out of 5 average rating, 41 reviewsLuxurious family retreat home in the mountains
31 Oct – 7 Nov
Weekly house rentals
Home in Barnard
4.92 out of 5 average rating, 141 reviewsCozy 2bd, Tennis Court, Steps to Lake, on 6 acres
2–9 Dec
Home in Roxbury
4.9 out of 5 average rating, 157 reviewsCaptain Tom's Cabin - Secluded Vermont Getaway
29 Sep – 6 Oct
Home in Tunbridge
4.98 out of 5 average rating, 315 reviewsThe Barnbrook House
16–23 Jan
Home in Woodstock
5.0 out of 5 average rating, 110 reviewsBeautiful Woodstock Home-Perfect for entertaining
17–24 Sep
Home in Newbury
4.97 out of 5 average rating, 114 reviewsWright’s Mountain Retreat with Sauna
31 Mar – 7 Apr
Home in Lincoln
4.98 out of 5 average rating, 172 reviewsModern Home in Lincoln on 13 ac W/ Lvl 2 Charger
5–12 May
Home in Hartford
4.95 out of 5 average rating, 130 reviewsThe Quechee Haus: VT Retreat with Outdoor Hot Tub
10–17 Dec
Home in Killington
4.88 out of 5 average rating, 215 reviewsTanglewood Vista Ski Home: Close|Hot Tub|Sauna|BBQ
14–21 May
Private house rentals
Home in Pittsfield
4.97 out of 5 average rating, 38 reviewsHideaway Mountain at Killington
8–15 Apr
Home in Pittsfield
4.86 out of 5 average rating, 90 reviewsA million-dollar view near Killington on 60 acres.
4–11 Aug
Home in Pittsfield
4.93 out of 5 average rating, 15 reviewsBeautiful Cabin w/Hot Tub by #1 Golf Course in VT
2–9 Dec
Home in Hancock
4.91 out of 5 average rating, 89 reviewsThe Branch House | between Sugarbush & Killington
21–28 Oct
Home in Rochester
5.0 out of 5 average rating, 42 reviewsSecluded Oasis: Sugarbush, Killington, Mtn Biking
17–24 Oct
Home in Barnard
4.98 out of 5 average rating, 90 reviewsThe Looking Glass, a modernistic escape
17–24 Feb
Home in Pittsfield
5.0 out of 5 average rating, 8 reviewsMountain Top - Fresh Pond - Killington - Hot Tub
8–15 Nov
Home in Pittsfield
4.9 out of 5 average rating, 20 reviewsThe Getaway, Killington. Four Bedroom with Hot Tub
15–22 Nov
Quick stats about house rentals in Pittsfield
Total rentals
30 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
1.4K reviews
Nightly prices starting at
€ 215 before taxes and fees
Destinations to explore
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