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, 133 reviewsUpstate Modern Scandinavian Barn in the Catskills
Home in Litchfield
4.93 out of 5 average rating, 166 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
Home in Woodstock
4.91 out of 5 average rating, 214 reviewsJapanese Teahouse & Onsen, outside shower, tennis
Home in Hudson
4.95 out of 5 average rating, 112 reviewsHudson Retreat w/HotTub, PlungePool+ OutdoorShower
Home in Cottekill
4.96 out of 5 average rating, 245 reviewsPeace & Privacy - High Falls (hot tub & salt pool)
Home in Richmond
4.96 out of 5 average rating, 23 reviewsEscape to The Berkshires w/Pool by Evergreen Home
Home in West Stockbridge
5.0 out of 5 average rating, 6 reviewsHeated Pool, Screened Porch, Gardens, Sleeps 13!
Home in Lee
4.98 out of 5 average rating, 63 reviewsBerkshire Vacation Home in Lee (Pool Opens in May)
Condo rentals with a pool
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
Condo in Windham
4.74 out of 5 average rating, 244 reviewsSummer getaway w/Pool & Tennis Court
Condo in Dover
4.99 out of 5 average rating, 100 reviewsWinter Dream! The Handle Lodge at Snowtree Condos
Condo in Dover
4.99 out of 5 average rating, 105 reviews*Summer Mountain Oasis: Base of Mount Snow Retreat
Condo in Dover
4.88 out of 5 average rating, 146 reviewsCozy condo with great views of Mt. Snow
Condo in Dover
4.87 out of 5 average rating, 222 reviewsMt Snow Ski In/Out at Seasons
Condo in Hancock
4.9 out of 5 average rating, 51 reviewsJiminy Peak Country Inn - ski in/out condo MT view
Condo in Hancock
4.95 out of 5 average rating, 19 reviewsUpscale 2 bed/2bath Condo at a Mountain Resort!
Home rentals with a private pool
Home in Lagrangeville
4.84 out of 5 average rating, 121 reviewsClassic Hudson Valley Farmhouse Nestled in 9 Rolling Acres
Home in Kerhonkson
4.94 out of 5 average rating, 326 reviewsCountry House: Rustic Charm With Modern Feel
Villa in Coxsackie
4.99 out of 5 average rating, 80 reviewsMagnificent Hudson River Estate with Infinity Pool and Spa
Home in Woodstock
4.6 out of 5 average rating, 10 reviewsLuxury Retreat in the Catskills
Home in Lanesville
4.77 out of 5 average rating, 205 reviewsGo Hiking and Skiing from a Family-Friendly Farmhouse
Home in Rhinebeck
5.0 out of 5 average rating, 65 reviewsRhinebeck Country Living with a Modern Twist
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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