Vacation rentals with a pool in Woodstock

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Woodstock

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

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Superhost

A serene outdoor scene features a reflecting pool surrounded by a grassy area. A wooden barn stands in the background, partially shaded, with a deck area furnished with lounge chairs. Lush greenery is visible in the surrounding landscape under a partly cloudy sky.

Tiny home in Ghent

4.95 out of 5 average rating, 131 reviews

Country Getaway Tiny House in Woods w/Pool/Sauna.

Tiny Small House - 600 Sq ft. of new living space on 30 private acres with walkable trains in Beautiful Columbia County. Secluded privacy surrounded by nature. House has everything you need and sleeps 4 with two twin loft beds. Enjoy the pool and renovated barn pool house. In the Winter stay warm by the wood stove. Enjoy the 6 person sauna year round. Restaurants close by or stay in and enjoy the property. Located 9 miles from Hudson and 3 miles from Chatham and Kinderhook. Near OMI Arts Center.

Guest favorite

The outdoor area showcases a seasonal heated pool surrounded by a safety fence. Colorful inflatable pool toys and a waterslide are visible. Sun loungers sit on a wooden deck, with lush greenery framing the space, creating a serene and inviting atmosphere for relaxation.

Home in Saugerties

4.94 out of 5 average rating, 68 reviews

Perfect Family Retreat•Pool•Volleyball•Firepit

This stylish, 3-bed, 2-bath home has a plethora of amenities that will keep the kids occupied for hours any time of the year, including a large kids play area in the lower level of the house and a large back yard w newly built FIREPIT area. Close to ski & a back field to build snowmen & sled in winter. In summer, a seasonal heated pool, waterslide & child safety fence, tree house, beach volleyball crt, swing set. Saugerties 10 mins. Relax with the whole family at this peaceful place to stay.

Guest favorite

Home in New Paltz

4.93 out of 5 average rating, 133 reviews

Harrison Field 10Acres Pool FirePit BikeRailTrail

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

A clear, blue saltwater swimming pool is surrounded by lush greenery and tall trees. Lounge chairs are positioned by the poolside, with a stone path leading to the water. The tranquil setting provides a sense of privacy and relaxation.

Home in Hudson

4.93 out of 5 average rating, 243 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

Top guest favorite

The exterior of a modern cabin is displayed, featuring large glass windows and a sleek black facade. A heated pool is visible with a smooth blue surface. Several lounge chairs are arranged around the pool, enhancing the outdoor relaxation space.

Cabin in Red Hook

4.96 out of 5 average rating, 348 reviews

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open May - October. During the colder months we recommend soaking in our giant freestanding tub, which easily fits two humans.] Welcome to Maitopia - our modern, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub for two, a floating fireplace for cozy winter moments and a heated pool. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without reviews.

Top guest favorite

A serene outdoor space features a private in-ground pool bordered by a travertine patio, accompanied by lounging chairs. A charming purple poolhouse stands nearby, while the multi-story house is illuminated under the evening sky, surrounded by lush greenery and vibrant flowers.

Townhouse in Hudson

4.95 out of 5 average rating, 209 reviews

Palazzo Hudson: Luxury Home with Pool, Spa, 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 & a separate poolhouse library lounge. A home for all seasons, you'll experience inspiration and relaxation from the warm, light-filled rooms, curated art, books, music, luxury spa features, and outdoor deck, patios, and gardens. A quick stroll to the restaurants, bars, cafes, and shops of Warren Street and the Upper Depot District.

Guest favorite

A large heated swimming pool is surrounded by lush greenery, with several lounge chairs arranged on a concrete deck. A float in blue and white lies on the water's surface, and an umbrella provides shade nearby.

Apartment in Saugerties

4.97 out of 5 average rating, 111 reviews

Lovely Creekside w pool/sauna near Woodstock

This 2-room apt overlooks a flowing stream and includes: bedroom, full kitchen, bath, living room, laundry, deck and use of large heated swimming pool. A beautiful setting very convenient to Woodstock and Saugerties - 3 miles from the NYS Thuway Exit 20, very close to HITS and 30 minutes from skiing at Hunter Mountain. We are carbon neutral, with geothermal and airsource heat pumps, large solar array, and a Level 2 EV charger for our guests. Nosotros hablamos un poco de español

Superhost

A central living space features a spiral staircase and high cathedral ceilings supported by wooden beams. Light streams through large windows, illuminating a mix of white sofas and chairs positioned on a natural fiber rug. The open layout connects to the kitchen area in the background.

Home in Stanfordville

5 out of 5 average rating, 5 reviews

The Round House w/ Heated Pool

Make some memories at this unique and family-friendly estate. Private & secluded on over 20 acres with heated inground pool this spacious 4 bed, 2 full baths, plus den with sleeping sofa has plenty of space for all. Park-like grounds featuring open fields, picturesque stonewalls overlooking beautiful, heated pool and expansive stone patio where you can entertain or just relax and enjoy nature. Discover effortless living in this fun yet chic dwelling in a remote natural setting.

Superhost

The image shows a serene cottage surrounded by lush greenery and rolling hills. A clear in-ground pool is positioned in the foreground, offering a glimpse of relaxation. The cottage features a charming façade under a bright sky, emphasizing the tranquility of the surrounding nature.

Home in Roxbury

4.8 out of 5 average rating, 5 reviews

Private Contemporary Cottage with Pool and Hot Tub

Follow the birch-lined road to this private getaway cottage. 💘12Min to Roxbury Barn and Estate 🛍️5 Min to Roxbury or Margaretville for all your shopping needs 💘18 Min to Stone Tavern Farm ⛷️20 Min to Plattekill Ski Mountain 💘18 Min to Inn at West Settlement venue 🚠25 Min to Belleayre Mountain Ski Center Great for Summer vacation with a heated pool, and the perfect retreat for any other time. Hot tub is available year round! A view that's incredible any time of year! 🍂❄️

Guest favorite

A serene saltwater pool is framed by lush greenery, providing a tranquil escape. Comfortable lounge chairs are positioned around the patio, inviting relaxation. The setting is peaceful, surrounded by trees that enhance the private atmosphere.

Home in Kerhonkson

4.95 out of 5 average rating, 354 reviews

Beautiful Salt Water Pool & Fully Fenced 10 Acres

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

A private saltwater pool is surrounded by lush greenery, featuring a smooth stone deck. The clear blue water invites relaxation, while steps lead into the pool. Trees provide natural shade along the perimeter, creating a serene outdoor setting.

Home in Woodstock

4.86 out of 5 average rating, 132 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 spacious studio cottage (with bathroom) & heat that can be used as a WFH private office. It has it's own high speed internet.

Guest favorite

A charming wooden studio cabin sits nestled among trees, surrounded by lush green grass. A set of steps leads to a private deck, furnished with a green umbrella, inviting guests to enjoy the serene outdoor views.

Home in Woodstock

4.91 out of 5 average rating, 199 reviews

Woodstock Romantic Mountain Studio w/ Pool

Come escape to the cozy Woodstock studio . Swim, hike, bike, BBQ and experience peace & serenity. Our large studio is a vacation gem and home away from home on 10 mountain top acres with large shared pool. 5 star. (Pool is shared with us, & we try to respect our guests privacy.) High-speed wifi Work remotely. The studio is on a private road just 5 mins from the center of Woodstock. Perfect for a couple, small family or single. 30 day rentals available October-May

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What guests are saying

Stunning Mntn Views• Heated Pool• H/Tub• Sauna

4.93 out of 5 average rating, 46 reviews2 weeks ago

My friends and I had a wonderful long weekend at Susanna's home! The location cannot be beat, beautiful view and close to town with lots of cute shops and great restaurants nearby. The hot tub and sauna were amazing, the entire place was so peaceful. The perfect retreat and would definitely rent again!

Home in New Paltz

What guests are saying

Private Cabin in the Woods w/ Hot Tub near Hudson

4.9 out of 5 average rating, 40 reviews1 month ago

Beautiful getaway in a quiet neighborhood with ability to easily walk to the Main Street with some restaurants. Great neighborhood to get a walk in! House had everything you need for cooking, provided plenty of cleaning products, garbage bags, etc, lots of towels (even for the hot tub!). Would recommend, especially for groups!

Cabin in Valatie

What guests are saying

Serenity Estate: Farmhouse+Cottage w Pool & HotTub

5 out of 5 average rating, 6 reviews3 months ago

Fouz & Chris were excellent hosts with an amazing property. From the time our booking was confirmed they were in contact with us to insure we had as comfortable a stay as possible. Check-in was simple and flexible. The house was great, clean and well equipped. Highly recommend.

Chalet in Shandaken

What guests are saying

Beaver | Pool, Firepit, Secluded, 10 acres

4.83 out of 5 average rating, 70 reviews2 months ago

We had an absolutely wonderful stay at Hava’s Airbnb! From the moment we booked, Hava was an incredible host—warm, welcoming, and unbelievably reachable. She responded to every question we had almost instantly, whether it was about check-in details or local recommendations, making the entire experience seamless and stress-free. The place itself was spotless, cozy, and exactly as described, with thoughtful touches that made us feel right at home. Hava’s communication stood out—she checked in to ensure everything was perfect without ever being intrusive. Her suggestions for nearby spots were spot-on, and it’s clear she genuinely cares about her guests’ comfort. We couldn’t have asked for a better host, and we’d love to stay here again. Highly recommend Hava to anyone looking for a fantastic Airbnb experience!

Home in Kingston

What guests are saying

Spirit Cabin: Lakefront w/Pool-Sauna-Cold Plunge

5 out of 5 average rating, 40 reviews3 weeks ago

Absolutely Perfect Stay in Forestburgh Our stay at the Spirit Cabin was nothing short of amazing. The home is stunning, with meticulous attention to detail in every corner. The breathtaking views made every moment feel special, and the entire space was super warm with welcoming atmosphere. We brought our dog along and had the best time- BBQ, kayaking, fire pit, sauna, hot tub, and in general - enjoying the beautiful spacious surroundings. The hosts thought of absolutely everything—there was a popcorn kit, a s’mores kit, and a mini bar stocked with everything needed for hot chocolate, tea, coffee and even mixers for cocktails. Every detail was carefully considered, making our stay feel effortless and luxurious. We truly can’t wait to go back! Highly recommend this place to anyone looking for a perfect getaway.

Cabin in Forestburgh

What guests are saying

Spacious Catskills Farmhouse w/ In-Ground Pool!

4.89 out of 5 average rating, 91 reviews2 months ago

This is a beautiful old house with huge windows and tons of light, beautiful views, and lots of bedrooms and hang out areas so everyone has space. The kitchen had everything we needed, the beds were comfortable and the entire place was super clean and tidy. There was a good selection of games we could play and music that our family enjoyed. It was also so nice that the house was pet friendly. The only downside was that the house was quite close to the road and my kids really wanted to sled down the hill in the backyard, but there was nothing to stop them from sliding into the road. There is hardly any traffic on the road, though, so noise was not an issue. We really enjoyed our stay here! Definitely recommend for big groups or families. We are a 7 person family - teenage kids, parents, grandparents.

Home in Grahamsville

What guests are saying

Catskill Home w/ Sauna, by ski &Mountain view

4.91 out of 5 average rating, 32 reviews3 months ago

Thank you so much for hosting us. Our family truly appreciated the easy access and the prompt responses to any questions we had. We had a wonderful time staying at the house and really enjoyed using the sauna. Everything was so clean, which made our experience even more enjoyable. We’re grateful for your hospitality and thoughtfulness!

Home in Preston-Potter Hollow

What guests are saying

Zen Minnewaska Retreat (Entire Home)

4.94 out of 5 average rating, 36 reviews6 months ago

Enjoyed our stay very much. House was very clean and neat. Private and wooded surroundings that were especially pretty in mid-October. The foosball table was a big hit with my kids. Great location, close to Minnewaska, Mohonk, Rough Cut Brewery and not too far from New Paltz main street either. Shani was very good with communication and clear instructions. When I messaged her with a question about the heat in the house, she responded right away and solved it for us. Would stay again!

Home in Kerhonkson

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