Vacation rentals with a pool in Rhinebeck

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Rhinebeck

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Townhouse in Hudson

4.95 out of 5 average rating, 201 reviews

Palazzo Hudson: Luxury Pool, Hot Tub, and Sauna

Welcome to Palazzo Hudson! The only private vacation home in the town of Hudson with a chef's kitchen, seasonal in-ground pool, deluxe sauna, cedar hot tub & the Blue Library-Lounge Barn. A home for all seasons, you'll experience inspiration and relaxation in the warm and whimsical spaces of our unique light-filled home's art, books, music, luxury spa features, outdoor patios, deck, and gardens. A quick stroll to restaurants, bars, cafes, and shops of Warren Street and the Upper Depot District.

Guest favorite

Townhouse in Windham

4.9 out of 5 average rating, 137 reviews

Amazing + pet friendly gem in the heart of Windham

Amazing 2 floor spacious getaway with A/C just minutes away from Windham Mountain ski resort, hiking trails, and great restaurants. Family friendly home with a large inviting living room, 2 spacious bedrooms, 2 full bathrooms and wood burning fireplace. Updated kitchen appliances, super-fast Wi-Fi and 3 smart TV's. Many extras including parking, 2 tennis courts, swimming pool and firepit. BBQ Grill on private back deck with scenic views. Winter season rentals preferred during Dec - March.

Guest favorite

Home in New Paltz

4.93 out of 5 average rating, 133 reviews

Harrison Field WeekendGetAway ApplePick Hike Bike

Our country getaway is nestled along the Walkill Rail Trail with stunning views of the ridge. Our home is a perfect retreat to relax and enjoy your time in the beautiful Hudson Valley. We have a fully appointed kitchen, large deck, heated pool, and massive 10 acres that will give you plenty of space to explore! We are centrally located to Minewaska, wineries, hiking, Hudson River Walkway, Storm King and so much more! You are guaranteed to make special memories with your friends and family!

Guest favorite

Cottage in Woodstock

4.8 out of 5 average rating, 112 reviews

Woodstock Mountain View Cottage near Ski & Dining

Our romantic 2 bed cottage has large beamed ceilings, fully stocked kitchen, bathtub, mountain views, & hiking trails. We use strict cleaning protocols to ensure every stay is perfect. The house is equipped with fast wifi & a ROKU Ultra for all of your tv needs! The house is just 3 minutes driving to the center of Woodstock. In summer, swim in our pool, hike a nearby trail, grill or relax in the hammock. Our pool is shared with us & it is a true summer oasis. Operating permit #21H-136

Guest favorite

Home in Kerhonkson

4.94 out of 5 average rating, 109 reviews

Modern Lux 5-Bed, Catskill view, Dog Friendly!

Beautifully renovated mid-century modern retreat! With 5 private bedrooms, 3.5 bathrooms, 2 spacious living rooms, a double-sided fireplace, and a mini grand piano, this space is perfect for families, groups, or couples seeking a romantic escape. Enjoy the seasonal heated saltwater pool in summer and relax in a dog-friendly, fenced area just under two hours from NYC via New Paltz. Experience breathtaking views and complete privacy in the stunning Kerhonkson area. The pool is now closed.

Guest favorite

Home in Hudson

4.93 out of 5 average rating, 242 reviews

Casa Luna Country Retreat with Pool, Hudson, NY

CASA LUNA Perfect peaceful upstate NY country retreat. An all year round escape. 2 hours from NYC driving or Amtrak. 15 mins to downtown Hudson with great restaurants and shopping. 20 mins to water skiing on Copake Lake and 25 mins snow skiing at Catamount, Berkshires. Private & secluded. Columbia County, New York. 4 bedrooms, 2.5 bathrooms, salt water swimming pool, koi pond, claw foot bath tub, steam room. If CASA LUNA is booked check CASA SOL https://www.airbnb.com/rooms/1627143

Guest favorite

Cabin in Shandaken

4.95 out of 5 average rating, 166 reviews

Cozy Catskills 4Br Retreat w/ FirePit & Hot Tub

7 min drive to Phoenicia 10 min drive to Belleayre Mountain 25 min drive to Hunter Mountain 35 min drive to Windham Mountain Renovated 1920’s cabin style home nestled on 4 acres in the Catskill Mountains. Easy to get to and conveniently located near great restaurants, skiing, hiking, tubing, fishing, and swimming holes. A ton of outdoor space to enjoy in addition to our fully private seasonal pool (Late May-mid Sept). Our newly added 6 person hot tub is available year round.

Guest favorite

Home in Stone Ridge

4.98 out of 5 average rating, 100 reviews

Stone Ridge Retreat with Heated Pool & Hot Tub

Our renovated home is situated on 4 acres of private property, just two hours north of NYC. The house is a short drive from Woodstock, the Catskills and Shawangunk mountains. It's perfect for any weekend get away or vacation with family and friends. The days are perfect for sightseeing while the nights are cool enough to enjoy our hot tub after a day spent hiking in the Catskills. My Pool is now closed until next summer. Terrific Wifi with speed up to 300 Mbps. Pets are allowed.

Superhost

Cabin in Ruby

4.9 out of 5 average rating, 105 reviews

Enchanting Upstate Cabin w Pool, Firepit

Welcome to our family-friendly haven in the heart of the beautiful Hudson Valley, just 10 minutes from Kingston, Saugerties, and Woodstock. Less than 2 hours from New York, our retreat offers an idyllic escape surrounded by enchanting forest views. Great for large groups, and year round stays with a heated pool and air conditioning in summer months. Just 40 mins away from skiing Hunter. Listing pics by @dirtandglass and @heypamcakes See more snapshots @theserenityhomes on IG.

Guest favorite

Home in Kerhonkson

4.95 out of 5 average rating, 345 reviews

Cozy Country Cabin for Dogs, Families & Friends

Look from the luxurious spa tub at the countryside oasis atop a rolling knoll on the edge of fir-scented forest land. Come home from a hike, farm, or award winning restaurant, & snuggle up by the fire under grand cathedral ceilings. In summer, swim in the salt water pool & enjoy the fire pit surrounded by lush landscaping & quiet. Stunning views as the seasons change, the windows showcasing rolling snowy hills or the vibrant colors of autumn leaves climbing the mountains.

Guest favorite

Home in Woodstock

4.85 out of 5 average rating, 121 reviews

Gorgeous Villa Mntn Views, salt H2O pool, hot tub!

Our beautiful Villa has amazing mountain views, a clean, modern design and is the perfect getaway to socialize & relax. It is ideally located for hiking & has a gorgeous, private salt water pool (mid May- mid Oct) and a wonderful hot tub which is open year round! Please check for pool opening/closing. In addition to the main house there is also a studio cottage (with bathroom) that can be used as a WFH private office. It has it's own high speed internet.

Guest favorite

Home in Ghent

4.88 out of 5 average rating, 301 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

Escape to our recently renovated guest house on a 12-acre property, 15min from Hudson. Take in the rural setting through oversized glass doors. Infared Sauna is within running distance of the swimming pond for a cold plunge. Located in a park like setting of rolling hills & colorful sugar maple trees. Fully equipped kitchen, memory foam mattress and all the amenities. In home Massage/Yoga available. XC ski from the house! 45min to downhill.