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 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
Oct 27 – Nov 3
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
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)
Sep 2 – 9
Home in Great Barrington
5.0 out of 5 average rating, 52 reviewsStunning luxury home with pool
Sep 28 – Oct 5
Condo rentals with a pool
Condo in Windham
4.74 out of 5 average rating, 243 reviewsSummer getaway w/Pool & Tennis Court
Aug 28 – Sep 4
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
May 28 – Jun 4
Condo in Dover
4.99 out of 5 average rating, 100 reviewsWinter Dream! The Handle Lodge at Snowtree Condos
Sep 7 – 14
Condo in Dover
4.99 out of 5 average rating, 105 reviews*Mountain Oasis: Base of Mount Snow Retreat*
Sep 22 – 29
Condo in Dover
4.88 out of 5 average rating, 146 reviewsCozy condo with great views of Mt. Snow
Oct 12 – 19
Condo in Dover
4.87 out of 5 average rating, 222 reviewsMt Snow Ski In/Out at Seasons
Sep 29 – Oct 6
Condo in Hancock
4.9 out of 5 average rating, 51 reviewsJiminy Peak Country Inn - ski in/out condo MT view
Sep 15 – 22
Condo in Hancock
4.95 out of 5 average rating, 19 reviewsUpscale 2 bed/2bath Condo at a Mountain Resort!
Oct 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
Apr 18 – 25
Home in Rhinebeck
5.0 out of 5 average rating, 65 reviewsRhinebeck Country Living with a Modern Twist
Sep 25 – Oct 2
Home in Lanesville
4.77 out of 5 average rating, 205 reviewsGo Hiking and Skiing from a Family-Friendly Farmhouse
Mar 7 – 14
Home in Woodstock
4.6 out of 5 average rating, 10 reviewsLuxury Retreat in the Catskills
Aug 25 – Sep 1
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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