Vacation rentals with a pool in Stockbridge
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Stockbridge
Guests agree: these homes with a pool 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 rentals with a pool
House rentals with a pool
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
Jan 6 – 13
Home in Cottekill
4.95 out of 5 average rating, 242 reviewsPeace & Privacy - High Falls (hot tub & salt pool)
Aug 23 – 30
Home in Saugerties
4.96 out of 5 average rating, 150 reviewsLux 1800's renovated farmhouse w/hot tub+pool
Oct 22 – 29
Home in Woodstock
4.91 out of 5 average rating, 211 reviewsJapanese Teahouse & Onsen, outside shower, tennis
Dec 31 – Jan 7
Home in Pine Plains
4.95 out of 5 average rating, 131 reviewsStylish, Secluded Getaway with Pool & Fireplace
May 27 – Jun 3
Home in Woodstock
4.91 out of 5 average rating, 192 reviewsGlenford Studio with Pool & Mountain Views
Jul 15 – 22
Home in Richmond
4.96 out of 5 average rating, 23 reviewsEscape to The Berkshires w/Pool by Evergreen Home
May 13 – 20
Home in Lee
4.98 out of 5 average rating, 62 reviewsBerkshire Vacation Home in Lee (Pool Opens in May)
Oct 21 – 28
Condo rentals with a pool
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
Jun 5 – 12
Condo in Windham
4.74 out of 5 average rating, 243 reviewsSummer getaway w/Pool & Tennis Court
Jun 22 – 29
Condo in Hancock
4.9 out of 5 average rating, 51 reviewsJiminy Peak Country Inn - ski in/out condo MT view
Sep 23 – 30
Condo in Hancock
4.95 out of 5 average rating, 19 reviewsUpscale 2 bed/2bath Condo at a Mountain Resort!
Dec 4 – 11
Condo in Hancock
4.9 out of 5 average rating, 21 reviewsAll-season Berkshires ski resort condo - Sitzmark
Jul 28 – Aug 4
Condo in Hancock
4.96 out of 5 average rating, 27 reviewsSKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit2
May 11 – 18
Condo in Windham
4.95 out of 5 average rating, 22 reviewsLovely stylish 2-bedroom condo with community pool
Apr 12 – 19
Condo in Hancock
4.93 out of 5 average rating, 15 reviewsLarge one bedroom, two full bath, full kitchen
Jul 12 – 19
Home rentals with a private pool
Villa in Coxsackie
4.99 out of 5 average rating, 80 reviewsMagnificent Hudson River Estate with Infinity Pool and Spa
Jan 23 – 30
Home in Rhinebeck
5.0 out of 5 average rating, 65 reviewsRhinebeck Country Living with a Modern Twist
Oct 3 – 10
Home in Lanesville
4.77 out of 5 average rating, 205 reviewsGo Hiking and Skiing from a Family-Friendly Farmhouse
Mar 14 – 21
Home in Woodstock
4.6 out of 5 average rating, 10 reviewsLuxury Retreat in the Catskills
Sep 2 – 9
Quick stats about vacation rentals with a pool in Stockbridge
Total rentals
30 properties
Wifi availability
30 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
300 reviews
Nightly prices starting at
$110 before taxes and fees
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