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 Egremont
4.97 out of 5 average rating, 112 reviewsA sunny, quiet chalet beautifully decorated.
Jan 15 – 22
Home in Pittsfield
4.98 out of 5 average rating, 102 reviewsHidden Oasis in the Mountains by Evergreen Home
Dec 31 – Jan 7
Home in Canaan
4.9 out of 5 average rating, 150 reviewsBerkshire Lakefront House with Amazing Views
Jan 3 – 10
Home in Great Barrington
4.96 out of 5 average rating, 139 reviewsElegant Year-Round Lakeside Retreat with AC
Dec 2 – 9
Home in Lenox
4.96 out of 5 average rating, 170 reviewsLenox - Walk to Town - Berkshire Home
Mar 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 1 – 8
Home in Stockbridge
4.95 out of 5 average rating, 91 reviewsBright Stockbridge country home, near everything!
Dec 25 – Jan 1
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
Dec 4 – 11
Home in Woodstock
4.98 out of 5 average rating, 100 reviewsWoodstock Historic Artist Estate- The Museum House
Jan 31 – Feb 7
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Sep 13 – 20
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
Oct 27 – Nov 3
Home in Woodstock
4.91 out of 5 average rating, 209 reviewsJapanese Teahouse & Onsen, outside shower, tennis
Dec 29 – Jan 5
Home in Cottekill
4.95 out of 5 average rating, 242 reviewsPeace & Privacy - High Falls (hot tub & salt pool)
Aug 30 – Sep 6
Home in Rhinebeck
4.96 out of 5 average rating, 164 reviewsOn The Hill in Rhinebeck
Dec 20 – 27
Home in woodstock
4.86 out of 5 average rating, 486 reviewsCABIN WITH HOT TUB OUTDOOR FIREPLACE PIZZA OVEN
Aug 13 – 20
House rentals with a hot tub
Home in Catskill
4.96 out of 5 average rating, 135 reviewsHEAVEN ON EARTH - Hudson Riverfront Home
Dec 8 – 15
Home in Colebrook
4.99 out of 5 average rating, 202 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Apr 2 – 9
Home in Otis
4.85 out of 5 average rating, 163 reviewsThe Meadows House @ Otis Ridge w/ 7-person hot tub
Nov 9 – 16
Home in High Falls
5.0 out of 5 average rating, 193 reviewsOur Place - A Big Little House
Jul 21 – 28
Home in Hudson
4.95 out of 5 average rating, 249 reviewsLivingston Farmhouse Escape with hot tub and sauna
Oct 8 – 15
Home in Catskill
4.95 out of 5 average rating, 139 reviewsHot Tub & Catskill hiking 15min from Hudson
Feb 19 – 26
Home in Saugerties
4.94 out of 5 average rating, 104 reviewsWaterfront Three bedroom in Saugerties w/ Hot Tub
Sep 25 – Oct 2
Home in Round Top
4.96 out of 5 average rating, 161 reviewsEscape in the Catskills w/hottub
May 15 – 22
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
G$20,908 GYD before taxes and fees
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