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 Chester
4.96 out of 5 average rating, 311 reviewsRiverfront Getaway
Sep 6 – 13
Home in Pittsfield
4.98 out of 5 average rating, 102 reviewsHidden Oasis in the Mountains by Evergreen Home
Dec 4 – 11
Home in Canaan
4.9 out of 5 average rating, 150 reviewsBerkshire Lakefront House with Amazing Views
Jan 1 – 8
Home in Rhinebeck
4.91 out of 5 average rating, 254 reviewsArchitectural wonder in the woods
Oct 2 – 9
Home in Lenox
4.96 out of 5 average rating, 170 reviewsLenox - Walk to Town - Berkshire Home
May 18 – 25
Home in Becket
4.94 out of 5 average rating, 36 reviewsNerd Preservation Sanctuary
Dec 16 – 23
Home in Lee
5.0 out of 5 average rating, 35 reviewsGreenHouse
Sep 9 – 16
Home in Stockbridge
4.94 out of 5 average rating, 90 reviewsBright Stockbridge country home, near everything!
Nov 9 – 16
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
Nov 12 – 19
Home in Woodstock
4.98 out of 5 average rating, 100 reviewsWoodstock Historic Artist Estate- The Museum House
Dec 30 – Jan 6
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, 435 reviewsmidcentury modern in ground pool walk 2 trail/town
Nov 26 – Dec 3
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
Nov 22 – 29
Home in Woodstock
4.91 out of 5 average rating, 209 reviewsJapanese Teahouse & Onsen, outside shower, tennis
Sep 20 – 27
Home in Litchfield
4.93 out of 5 average rating, 162 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
Sep 12 – 19
Home in Cottekill
4.95 out of 5 average rating, 241 reviewsPeace & Privacy - High Falls (hot tub & salt pool)
Sep 9 – 16
House rentals with a hot tub
Home in Great Barrington
4.96 out of 5 average rating, 139 reviewsElegant Year-Round Lakeside Retreat with AC
Mar 28 – Apr 4
Home in Catskill
4.96 out of 5 average rating, 135 reviewsHEAVEN ON EARTH - Hudson Riverfront Home
Apr 6 – 13
Home in Mount Tremper
4.94 out of 5 average rating, 172 reviewsThe Mountain Wonder - Hot tub, sauna, great views
Nov 28 – Dec 5
Home in Colebrook
4.99 out of 5 average rating, 202 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Mar 22 – 29
Home in Otis
4.85 out of 5 average rating, 162 reviewsThe Meadows House @ Otis Ridge w/ 7-person hot tub
Nov 9 – 16
Home in Hudson
4.95 out of 5 average rating, 249 reviewsLivingston Farmhouse Escape with hot tub and sauna
Oct 8 – 15
Home in Saugerties
4.95 out of 5 average rating, 103 reviewsWaterfront Three bedroom in Saugerties w/ Hot Tub
Sep 22 – 29
Home in High Falls
5.0 out of 5 average rating, 193 reviewsOur Place - A Big Little House
Oct 16 – 23
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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- Family travel hub Tips and inspiration
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