House holiday rentals in Stockbridge
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Top-rated house rentals in Stockbridge
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Stockbridge
House rentals with a pool
Home in Killington
4.92 out of 5 average rating, 165 reviewsCozy Condo Tucked in the Heart of Killington
21–28 Jun
Home in Mendon
4.88 out of 5 average rating, 210 reviewsRanch at Mendon Mt Orchards
22–29 Oct
Home in Plainfield
4.89 out of 5 average rating, 119 reviewsHistoric Home on 17 acres of land. Go escape!
5–12 Nov
Home in Peru
4.92 out of 5 average rating, 139 reviewsBeautiful Bromley/Manchester VT Retreat w/hot tub
21–28 Feb
Home in Salem
4.98 out of 5 average rating, 180 reviewsMagical Farm Getaway - a must visit!
12–19 Nov
Home in Warren
4.81 out of 5 average rating, 107 reviewsCharming Sugarbush Standalone Condo
15–22 May
Home in Killington
5.0 out of 5 average rating, 31 reviewsBearmont! Pool, HotTub, AC, FirePit
2–9 Jun
Home in Killington
5.0 out of 5 average rating, 28 reviews* Slope Side Sauna w/ Shuttle *
11–18 Jul
Weekly house rentals
Home in Rutland
5.0 out of 5 average rating, 121 reviewsONE ROOM SCHOOL HOUSE
5–12 Apr
Home in Hartford
4.95 out of 5 average rating, 130 reviewsThe Quechee Haus: VT Retreat with Outdoor Hot Tub
2–9 Sep
Home in Danby
4.97 out of 5 average rating, 198 reviewsComfortable farmhouse with stunning views
29 May – 5 Jun
Home in Ripton
4.89 out of 5 average rating, 257 reviewsCozy cottage near nature
22–29 Aug
Home in Fairlee
4.96 out of 5 average rating, 411 reviewsCozy Bow House Perched in Trees w/ Hot Tub & View
22–29 Apr
Home in Newbury
4.97 out of 5 average rating, 114 reviewsWright’s Mountain Retreat with Sauna
31 Mar – 7 Apr
Home in S Londonderry
4.95 out of 5 average rating, 270 reviewsCozy barn apartment in So. Vermont
19–26 Dec
Home in Barnard
4.88 out of 5 average rating, 113 reviewsBarnard Brickhouse
12–19 Apr
Private house rentals
Home in Barnard
4.98 out of 5 average rating, 90 reviewsThe Looking Glass, a modernistic escape
17–24 Feb
Home in Stockbridge
4.88 out of 5 average rating, 16 reviewsFarmhouse Cabin
2–9 Mar
Home in Bethel
4.95 out of 5 average rating, 84 reviewsComfortable 3 Bedroom King size Master w/ En suite
17–24 Feb
Home in Woodstock
5.0 out of 5 average rating, 10 reviewsWinterfound Farm - renovated VT barn & farm stay
7–14 Nov
Home in Bethel
4.93 out of 5 average rating, 42 reviews150 acres of serenity at Light Hill in Barnard, VT
15–22 Jun
Home in Rochester
5.0 out of 5 average rating, 42 reviewsSecluded Oasis: Sugarbush, Killington, Mtn Biking
18–25 Oct
Home in West Windsor
4.96 out of 5 average rating, 56 reviewsBirdie's Nest Guesthouse
22–29 Nov
Home in Pittsfield
5.0 out of 5 average rating, 8 reviewsMountain Top - Fresh Pond - Killington - Hot Tub
26 May – 2 Jun
Quick stats about house rentals in Stockbridge
Total rentals
50 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
1.7K reviews
Nightly prices starting at
€ 103 before taxes and fees
Destinations to explore
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