House vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Pittsfield house rentals
House rentals with a pool
Home in Killington
4.92 out of 5 average rating, 165 reviewsCozy Condo Tucked in the Heart of Killington
Jul 5 – 12
Home in Mendon
4.88 out of 5 average rating, 210 reviewsRanch at Mendon Mt Orchards
Sep 18 – 25
Home in Plainfield
4.89 out of 5 average rating, 119 reviewsHistoric Home on 17 acres of land. Go escape!
Dec 8 – 15
Home in Peru
4.92 out of 5 average rating, 139 reviewsBeautiful Bromley/Manchester VT Retreat w/hot tub
Sep 2 – 9
Home in Salem
4.98 out of 5 average rating, 180 reviewsMagical Farm Getaway - a must visit!
Nov 14 – 21
Home in Warren
4.81 out of 5 average rating, 107 reviewsCharming Sugarbush Standalone Condo
May 9 – 16
Home in Killington
4.97 out of 5 average rating, 30 reviewsSnowflake- Pool, Hot Tub, Wood Burning Fireplace
Oct 22 – 29
Home in Killington
5.0 out of 5 average rating, 28 reviews* Slope Side Sauna w/ Shuttle *
Sep 18 – 25
Weekly house rentals
Home in Ripton
4.89 out of 5 average rating, 257 reviewsCozy cottage near nature
Aug 23 – 30
Home in Montpelier
4.97 out of 5 average rating, 291 reviewsCozy, sunny apt. in Montpelier, Vt.
Aug 27 – Sep 3
Home in Woodstock
5.0 out of 5 average rating, 110 reviewsBeautiful Woodstock Home-Perfect for entertaining
Sep 17 – 24
Home in Tunbridge
4.98 out of 5 average rating, 316 reviewsThe Barnbrook House
Jan 5 – 12
Home in Fairlee
4.96 out of 5 average rating, 412 reviewsCozy Bow House Perched in Trees w/ Hot Tub & View
Jan 14 – 21
Home in Roxbury
4.9 out of 5 average rating, 157 reviewsCaptain Tom's Cabin - Secluded Vermont Getaway
Oct 8 – 15
Home in Newbury
4.97 out of 5 average rating, 114 reviewsWright’s Mountain Retreat with Sauna
Nov 1 – 8
Home in Hartford
4.95 out of 5 average rating, 130 reviewsThe Quechee Haus: VT Retreat with Outdoor Hot Tub
Nov 10 – 17
Private house rentals
Home in Pittsfield
4.97 out of 5 average rating, 38 reviewsHideaway Mountain at Killington
Apr 11 – 18
Home in Pittsfield
4.86 out of 5 average rating, 90 reviewsA million-dollar view near Killington on 60 acres.
Aug 6 – 13
Home in Rochester
4.97 out of 5 average rating, 89 reviewsBill’s Barn Rochester Vermont 3 Bdrm entire house
Jun 13 – 20
Home in Hancock
4.91 out of 5 average rating, 89 reviewsThe Branch House | between Sugarbush & Killington
Sep 9 – 16
Home in Pittsfield
4.93 out of 5 average rating, 15 reviewsBeautiful Cabin w/Hot Tub by #1 Golf Course in VT
Dec 4 – 11
Home in Rochester
5.0 out of 5 average rating, 42 reviewsSecluded Oasis: Sugarbush, Killington, Mtn Biking
Oct 20 – 27
Home in Barnard
4.98 out of 5 average rating, 90 reviewsThe Looking Glass, a modernistic escape
Feb 17 – 24
Home in Pittsfield
5.0 out of 5 average rating, 8 reviewsMountain Top - Fresh Pond - Killington - Hot Tub
Jun 13 – 20
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
G$48,030 GYD before taxes and fees
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