Holiday 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.
Holiday 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 Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
13–20 Sep
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
31 Oct – 7 Nov
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
7–14 May
Home in Woodstock
4.91 out of 5 average rating, 210 reviewsJapanese Teahouse & Onsen, outside shower, tennis
29 Dec – 5 Jan
Home in Litchfield
4.93 out of 5 average rating, 163 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
12–19 Sep
Home in Rhinebeck
4.96 out of 5 average rating, 164 reviewsOn The Hill in Rhinebeck
20–27 Dec
Home in Cottekill
4.95 out of 5 average rating, 242 reviewsPeace & Privacy - High Falls (hot tub & salt pool)
30 Aug – 6 Sep
Home in Great Barrington
5.0 out of 5 average rating, 52 reviewsStunning luxury home with pool
28 Sep – 5 Oct
Apartment rentals with a pool
Apartment in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
30 May – 6 Jun
Apartment in Hancock
4.9 out of 5 average rating, 51 reviewsJiminy Peak Country Inn - ski in/out condo MT view
17–24 Sep
Apartment in New Britain
4.87 out of 5 average rating, 39 reviewsBeautiful Space All For You!
23–30 Oct
Apartment in Hancock
4.95 out of 5 average rating, 19 reviewsUpscale 2 bed/2bath Condo at a Mountain Resort!
12–19 Oct
Apartment in Tannersville
5.0 out of 5 average rating, 34 reviewsModern 3BR Townhouse Minutes from Ski & Trails
3–10 Aug
Apartment in Hancock
4.96 out of 5 average rating, 27 reviewsSki - IN ski - out Lift&MT.VIEWS GR8 4 Season LOC.Unit2
3–10 May
Apartment in East Jewett
4.97 out of 5 average rating, 94 reviewsMountain&PondView2BRCondoFireplace
1–8 Jan
Apartment in Hancock
4.9 out of 5 average rating, 21 reviewsAll-season Berkshires ski resort condo - Sitzmark
22–29 May
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
22–29 Sep
Villa in Coxsackie
4.99 out of 5 average rating, 80 reviewsMagnificent Hudson River Estate with Infinity Pool and Spa
1–8 Jan
Home in Rhinebeck
5.0 out of 5 average rating, 65 reviewsRhinebeck Country Living with a Modern Twist
7–14 Sep
Home in Woodstock
4.6 out of 5 average rating, 10 reviewsLuxury Retreat in the Catskills
26 Aug – 2 Sep
Quick stats about holiday 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
₹8,341 before taxes and fees
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