Vacation rentals with a pool in Great Barrington
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Great Barrington
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 Great Barrington 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
Oct. 27 – Nov. 3
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Sep. 13 – 20
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
Jun. 23 – 30
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 Rhinebeck
4.96 out of 5 average rating, 164 reviewsOn The Hill in Rhinebeck
Sep. 20 – 27
Home in Cottekill
4.95 out of 5 average rating, 241 reviewsPeace & Privacy - High Falls (hot tub & salt pool)
Sep. 9 – 16
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 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. 15 – 22
Condo in Tannersville
5.0 out of 5 average rating, 34 reviewsModern 3BR Townhouse Minutes from Ski & Trails
Aug. 6 – 13
Condo in New Britain
4.87 out of 5 average rating, 39 reviewsBeautiful Space All For You!
Jun. 24 – Jul. 1
Condo in East Jewett
4.97 out of 5 average rating, 94 reviewsMountain&PondView2BRCondoFireplace
Oct. 5 – 12
Condo in Windham
4.95 out of 5 average rating, 22 reviewsLovely stylish 2-bedroom condo with community pool
Apr. 4 – 11
Home rentals with a private pool
Home in Lagrangeville
4.84 out of 5 average rating, 120 reviewsClassic Hudson Valley Farmhouse Nestled in 9 Rolling Acres
Sep. 23 – 30
Home in Kerhonkson
4.94 out of 5 average rating, 325 reviewsCountry House: Rustic Charm With Modern Feel
May 16 – 23
Home in Lanesville
4.77 out of 5 average rating, 205 reviewsGo Hiking and Skiing from a Family-Friendly Farmhouse
May 11 – 18
Home in Rhinebeck
5.0 out of 5 average rating, 65 reviewsRhinebeck Country Living with a Modern Twist
Sep. 25 – Oct. 2
Home in Woodstock
4.6 out of 5 average rating, 10 reviewsLuxury Retreat in the Catskills
Aug. 24 – 31
Quick stats about vacation rentals with a pool in Great Barrington
Total rentals
30 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
550 reviews
Nightly prices starting at
$137 CAD before taxes and fees
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