Vacation rentals with a pool in The Berkshires
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in The Berkshires
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 The Berkshires rentals with a pool
House rentals with a pool
Home in Stormville
4.94 out of 5 average rating, 156 reviewsPrivate Hudson Valley Country Retreat
Home in Gloversville
4.97 out of 5 average rating, 317 reviewsIndoor Heated Pool in the Adirondacks
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Home in Cold Spring
4.95 out of 5 average rating, 152 reviewsCozy, Modern Retreat in the Woods of Cold Spring
Home in Woodstock
4.91 out of 5 average rating, 214 reviewsJapanese Teahouse & Onsen, outside shower, tennis
Home in Pound Ridge
5.0 out of 5 average rating, 127 reviewsPeaceful Light-Filled Guesthouse 1 Hour From NYC
Home in Cheshire
5.0 out of 5 average rating, 120 reviewsPool House
Home in Saugerties
5.0 out of 5 average rating, 133 reviewsUpstate Modern Scandinavian Barn in the Catskills
Condo rentals with a pool
Condo in Windham
4.89 out of 5 average rating, 136 reviewsCozy Mountain hideaway Windham, Hunter
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
Condo in Norwich
4.9 out of 5 average rating, 147 reviewsRenovated Condo rental at Norwich inn villa & Spa
Condo in Norwich
4.99 out of 5 average rating, 104 reviewsJacuzzi/Sauna/Pool, On-site Spa, 3-mins to Mohegan
Condo in Norwich
4.88 out of 5 average rating, 211 reviewsThe N-V ...The Spa at the Norwich Inn.
Condo in Norwich
4.99 out of 5 average rating, 172 reviewsModern & Cozy Villa with low cleaning charge!
Condo in Dover
4.99 out of 5 average rating, 100 reviewsWinter Dream! The Handle Lodge at Snowtree Condos
Condo in Norwich
4.99 out of 5 average rating, 121 reviewsPeaceful Oasis steps from Mohegan Sun
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, 327 reviewsCountry House: Rustic Charm With Modern Feel
Farm stay in Fleischmanns
4.91 out of 5 average rating, 11 reviewsEscape to a Dreamy 1857 Farmhouse in Fleischmanns
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
Destinations to explore
- Rentals with pools United States
- Rentals with pools Long Island
- Rentals with pools New York
- Cabin rentals The Berkshires
- Beachfront rentals The Berkshires
- Luxury rentals The Berkshires
- Lake house rentals The Berkshires
- Fitness-friendly rentals The Berkshires
- Waterfront rentals The Berkshires
- Pet-friendly rentals The Berkshires
- Farmstay rentals The Berkshires
- Vacation home rentals The Berkshires
- Rentals with a home theater The Berkshires
- Rentals with a washer and dryer The Berkshires
- Rentals with a hot tub The Berkshires
- Family-friendly rentals The Berkshires
- Private suite rentals The Berkshires
- Smoking-friendly rentals The Berkshires
- Rentals with an EV charger The Berkshires
- Rentals with a kayak The Berkshires
- Townhouse rentals The Berkshires
- House rentals The Berkshires
- Boutique hotel rentals The Berkshires
- Apartment rentals The Berkshires
- Hotel rentals The Berkshires
- Bed and breakfasts The Berkshires
- Rentals with lake access The Berkshires
- Rentals with a firepit The Berkshires
- Guesthouse rentals The Berkshires
- Ski-in/ski-out rentals The Berkshires
- Aparthotel rentals The Berkshires
- Rentals with beach access The Berkshires
- Rentals with a fireplace The Berkshires
- Rentals with breakfast The Berkshires
- Rentals with an accessible height toilet The Berkshires
- Cottage rentals The Berkshires
- Rentals with a patio The Berkshires
- Rentals with outdoor seating The Berkshires
- Wheelchair accessible rentals The Berkshires
- Kid-friendly rentals The Berkshires
- Rentals with a sauna The Berkshires
- Monthly Rentals The Berkshires
- Chalet rentals The Berkshires
- Condo rentals The Berkshires
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom