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 Ghent
4.87 out of 5 average rating, 270 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
8–15 Dec
Home in Woodstock
4.98 out of 5 average rating, 100 reviewsWoodstock Historic Artist Estate- The Museum House
27 Dec – 3 Jan
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
13–20 Sept
Home in New Paltz
4.98 out of 5 average rating, 436 reviewsmidcentury modern in ground pool walk 2 trail/town
14–21 Jul
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
13–20 Jan
Home in Litchfield
4.93 out of 5 average rating, 163 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
12–19 Sept
Home in Woodstock
4.91 out of 5 average rating, 211 reviewsJapanese Teahouse & Onsen, outside shower, tennis
29 Dec – 5 Jan
Home in Cottekill
4.95 out of 5 average rating, 242 reviewsPeace & Privacy - High Falls (hot tub & salt pool)
2–9 Oct
Weekly house rentals
Home in New Paltz
4.97 out of 5 average rating, 680 reviewsVictorian Haven
19–26 Apr
Home in Lenox
4.96 out of 5 average rating, 170 reviewsLenox - Walk to Town - Berkshire Home
15–22 Nov
Home in Canaan
4.9 out of 5 average rating, 150 reviewsBerkshire Lakefront House with Amazing Views
7–14 Jan
Home in Becket
4.95 out of 5 average rating, 37 reviewsNerd Preservation Sanctuary
18–25 Sept
Home in Stockbridge
4.95 out of 5 average rating, 91 reviewsBright Stockbridge country home, near everything!
25 Dec – 1 Jan
Home in Lee
5.0 out of 5 average rating, 36 reviewsGreenHouse
4–11 Sept
Home in Stockbridge
5.0 out of 5 average rating, 32 reviewsRelaxing Berkshire Retreat with Lake Access
12–19 Sept
Home in Otis
4.83 out of 5 average rating, 60 reviewsSpringtime Oasis in the Berkshires!
2–9 Jun
Private house rentals
Home in West Stockbridge
5.0 out of 5 average rating, 54 reviewsHeart of the Berkshires - Bright, Cozy, Near Lake
31 May – 7 Jun
Home in Lee
4.97 out of 5 average rating, 70 reviewsStylish Mid-century Modern Berkshires Cape
19–26 May
Home in West Stockbridge
4.98 out of 5 average rating, 57 reviewsBerkshires-Enjoy The Peak, private home
1–8 Sept
Home in West Stockbridge
4.97 out of 5 average rating, 59 reviewsPanoramic Views, Indoor Pool by Evergreen Home
30 May – 6 Jun
Home in Chatham
4.98 out of 5 average rating, 97 reviewsHilltop studio apartment on 100 acres near village
22–29 May
Home in Richmond
5.0 out of 5 average rating, 56 reviewsLUXURY BERKSHIRES BARN! GRAND! VIEWS! 2/2
10–17 Mar
Home in Great Barrington
5.0 out of 5 average rating, 68 reviewsGranite Ledge, Modern home in a unique setting
12–19 Jan
Home in Great Barrington
5.0 out of 5 average rating, 19 reviewsNewly remodeled home with all the modern amenities
8–15 Nov
Quick stats about house rentals in Stockbridge
Total rentals
60 properties
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
50 properties are a good fit for families
Total number of reviews
2.3K reviews
Nightly prices starting at
£80 before taxes and fees
Destinations to explore
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