House vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Stockbridge house rentals
House rentals with free parking
Home in Lenox
4.96 out of 5 average rating, 170 reviewsLenox - Walk to Town - Berkshire Home
Apr 2 – 9
Home in Egremont
4.97 out of 5 average rating, 112 reviewsA sunny, quiet chalet beautifully decorated.
Apr 16 – 23
Home in Canaan
4.9 out of 5 average rating, 150 reviewsBerkshire Lakefront House with Amazing Views
Jan 9 – 16
Home in Catskill
4.96 out of 5 average rating, 136 reviewsHEAVEN ON EARTH - Hudson Riverfront Home
Sep 21 – 28
Home in Becket
4.95 out of 5 average rating, 37 reviewsNerd Preservation Sanctuary
Dec 10 – 17
Home in Stockbridge
4.95 out of 5 average rating, 91 reviewsBright Stockbridge country home, near everything!
Dec 23 – 30
Home in Lee
5.0 out of 5 average rating, 36 reviewsGreenHouse
Oct 15 – 22
Home in Stockbridge
4.98 out of 5 average rating, 86 reviewsGreek Revival Farmhouse
Mar 16 – 23
House rentals with a pool
Home in Ghent
4.87 out of 5 average rating, 271 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Mar 22 – 29
Home in Woodstock
4.98 out of 5 average rating, 101 reviewsWoodstock Historic Artist Estate- The Museum House
Sep 6 – 13
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Sep 13 – 20
Home in New Paltz
4.98 out of 5 average rating, 437 reviewsmidcentury modern in ground pool walk 2 trail/town
Jul 14 – 21
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
Nov 6 – 13
Home in Kerhonkson
4.94 out of 5 average rating, 325 reviewsCountry House: Rustic Charm With Modern Feel
Sep 10 – 17
Home in Cottekill
4.95 out of 5 average rating, 242 reviewsPeace & Privacy - High Falls (hot tub & salt pool)
Aug 23 – 30
Home in Litchfield
4.93 out of 5 average rating, 163 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
Sep 12 – 19
House rentals with a hot tub
Home in Chester
4.96 out of 5 average rating, 312 reviewsRiverfront Getaway
Nov 8 – 15
Home in Great Barrington
4.96 out of 5 average rating, 140 reviewsElegant Year-Round Lakeside Retreat with AC
Nov 26 – Dec 3
Home in Pittsfield
4.98 out of 5 average rating, 102 reviewsHidden Oasis in the Mountains by Evergreen Home
Oct 30 – Nov 6
Home in Colebrook
4.99 out of 5 average rating, 203 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Nov 7 – 14
Home in Otis
4.85 out of 5 average rating, 164 reviewsThe Meadows House @ Otis Ridge w/ 7-person hot tub
Nov 14 – 21
Home in High Falls
5.0 out of 5 average rating, 193 reviewsOur Place - A Big Little House
May 31 – Jun 7
Home in Saugerties
4.94 out of 5 average rating, 107 reviewsWaterfront Three bedroom in Saugerties w/ Hot Tub
Sep 19 – 26
Home in West Hurley
4.99 out of 5 average rating, 139 reviewsThe Monarch | Modern luxury | hot tub, firepit
Sep 25 – Oct 2
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
$100 before taxes and fees
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