Vacation rentals with a pool in Ulster

4.95 out of 5 average rating, 131 reviews

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

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

NataliaRating, 5 stars6 months ago

House was very clean and comfortable. Loved the decor and bed was super comfortable and cosy. Everything was there in the house- kitchen, bathroom, hot water. Well styled decor. Spotless. Felt very private and peaceful. Location was not as picturesque as I prefer, but fairly close to sight seeing.

4.83 out of 5 average rating, 201 reviews

A private in-ground heated pool is surrounded by lush greenery and trees. The water is a clear blue, reflecting the bright sky. A spacious wooden deck offers space for lounging, while garden lights are positioned to enhance the outdoor setting.

Cabin in Swan Lake

Stunning Sullivan County Cabin w/HotTub/Spa &Pool

CarolineRating, 5 stars3 weeks ago

Our group had a great time at Anna’s place. Spacious and comfortable with great views. Anna is very responsive and gave clear check in instructions. Little communication needed given her detailed instructions, and the little communication needed- she was very responsive.

4.94 out of 5 average rating, 68 reviews

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

Perfect Family Retreat•Pool•Volleyball•Firepit

YuliaRating, 5 stars2 months ago

We stayed as a family of 4, including a 1 year old and 3.5 year old. The place was extremely comfortable and had everything we would need for our stay. The kids enjoyed the playroom and kids room with lot of toys and books. Kitchen was fully stocked with plates, utensils, cooking ware, and a high chair. Place could easily accommodate more people, very clean, comfy beds. Property manager was very responsive. Short drive to downtown area. Lastly, great outdoor area, we’d love to plan a trip there when warmer as well!

4.96 out of 5 average rating, 348 reviews

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

Modern Upstate Cabin, near Rhinebeck NY

RichRating, 5 stars4 days ago

Tina’s place is fabulous. The modern decor and architecture is beautiful. The location is peaceful and the fenced in yard was amazing; our dog loved roaming around and exploring. The outdoor space is great for grilling and sitting around the fire pit. We especially loved the kitchen. It is fully appointed and the kitchen island is incredible for prep and serving. The washer dryer combo was an excellent touch and we were able to do a couple of quick washes so that everything was clean and ready to unpack at home. Saving the best for last; the soaker tub in the master bedroom is luxurious and relaxing. Thank you, Tina. We can’t wait to visit again soon.

4.95 out of 5 average rating, 210 reviews

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

Palazzo Hudson: Luxury Home with Pool, Spa, Sauna

LindaRating, 5 stars4 days ago

This was a wonderful getaway for our family of 5. Sienna obviously knows how to host guests. We felt special from the moment we stepped into her home. There were complimentary pastries and fresh bread and other local treats waiting for us. Everything was decorated beautifully. The Sauna and the hot tub were perfect! The library felt so special. And Sienna was quick to respond to any questions we might have had. We had an amazing time! Thank you so much!

4.97 out of 5 average rating, 111 reviews

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

Lovely Creekside w pool/sauna near Woodstock

MelissaRating, 5 stars8 months ago

We spent three nights at Rich and Sheila's place and it was an amazing getaway. Our apartment was perfect-clean and comfy. We loved the proximity to the creek and the pool was a huge bonus! Rich and Sheila were both responsive and welcoming. We look forward to a return trip.

5 out of 5 average rating, 5 reviews

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

The Round House w/ Heated Pool

JonathanRating, 5 stars5 months ago

An amazing location when you want to get slightly off the grid for peace and tranquility. Everything you need to truly slow down, dial out and get peace, quiet and rest. An amazing spot for a weekend getaway. If you want to find yourself amongst serene surroundings and a quiet, private wooded area, this is the place. Just enough modern amenities to be comfortable, but just basic enough to make you slow down. Tanner the host was the most responsive and helpful host of any of the airbnbs we've ever stayed. Truly went above and beyond at every turn to make our stay as comfortable as possible. More than accommodating with every request.

4.8 out of 5 average rating, 5 reviews

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

Private Contemporary Cottage with Pool and Hot Tub

ZacharyRating, 5 stars3 months ago

This house is a gem. Admittedly it’s far from home if you are coming from NYC, which is where my family is. However, the upside is that this house is beautiful, on a big private area, and the absolute perfect place for a getaway with kids. We were three families with three little girls who hopefully made forever memories. I hope we will be back again soon!

4.95 out of 5 average rating, 354 reviews

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

Beautiful Salt Water Pool & Fully Fenced 10 Acres

JongRating, 5 stars5 days ago

If you're looking for a stay off the beaten track this place is perfect - so much so that there is no cell signal so be warned! We even saw deer roaming the huge front yard(?) It is very child friendly, they have toys, high chair, crib and a stroller for use which reduced the amount of stuff we had to take. The only slight downside (to be expected) is the hot water tank is only 40 gallons and takes around 45mins to fill up so as a family of 5 we had to time the dishwasher, washing machine, bath time and showers carefully. Hosts are super responsive and were on hand to answer any questions.

4.86 out of 5 average rating, 132 reviews

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

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

HelaRating, 5 stars1 month ago

Beautiful home with amazing views. The house was very clean and spacious, the views were amazing. Susanna was very responsive and gave clear instructions. We had a very relaxing weekend and enjoyed very much staying at the house. We would love to come back.

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What guests are saying

Storybook Estate, Views, Hot Tub, Pool, Fire Pit

4.98 out of 5 average rating, 54 reviews3 months ago

My family and I (total 7 people) visited in Jan over a long weekend. We had a wonderful stay. The house looks even better than the pictures and was so clean. We loved the decor and discovered something new each day. Fouz and Chris are very thoughtful with the amenities and even left supplies for smores and some wine for us upon arrival. They gave helpful recommendations and were very responsive with any questions we had. We didn’t have any issues at all and would like to visit again in warmer months. Would definitely recommend.

Cabin in Prattsville

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 reviews2 months 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

Exquisite family friendly home with heated pool!

5 out of 5 average rating, 4 reviews9 months ago

We had a wonderful family vacation staying at Stone Hill. The house is absolutely perfect, literally a dream house. The pool and landscaping are beautiful and peaceful. The kitchen has everything you could ever need for cooking big meals. We thoroughly enjoyed the basket with s’mores ingredients and the fire pit. The screened-in porch was the perfect spot to enjoy morning coffee and look out at the scenery and pool. The ping-pong table in the basement was fun for the whole family, as well as a great selection of games and cards in the TV room. These came in handy on our 2 rainy days. The owner was super responsive to a few questions we had. It’s the perfect location, only a short drive to Great Barrington and grocery shopping at Guido’s. There’s also a great dog park in GB if you’re traveling with a dog. We hope to come back to Stone Hill many times in the future.

Home in Egremont

What guests are saying

The Dahlia Villa within Westerhall Gardens

5 out of 5 average rating, 23 reviews6 months ago

This is an exceptional property in every way, and provided an amazing weekend getaway for us. The design sense, amenities and attention to detail are all exquisite, inside and out. The cabin itself is lovely, somehow both modern and rustic, and the grounds with pond, landscaping and art pieces make for a lovely setting (including for dog walks). The location provides a great central hub, including hiking at Wonder Lake State Park literally 5 minutes away. We also went antiquing in Newburgh and shopping/dining in Cold Spring, both 20-30 minutes away. Lisa and Billy are considerate and friendly hosts, making clear they are available but not at all intrusive. We highly recommend this location.

Vacation home in Holmes

What guests are saying

Serene Country home 24 mi Mohawk ski area

4.94 out of 5 average rating, 32 reviews1 month ago

A beautiful home- super comfortable and spacious. It is outfitted with everything you could need. Peaceful location (we stayed in spring/winter- can’t speak to what it would be like in season). Lovely views. Easy to get into town by car (3-5 minutes!). Host was excellent - responsive to any questions or inquiries

Home in New Milford

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

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

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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Popular amenities for Ulster rentals with a pool

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House rentals with a pool

4.98 out of 5 average rating, 58 reviews

An in-ground pool surrounded by a stone patio is visible, with clear blue water reflecting the sky. Green trees and shrubs are present in the background, enhancing the natural setting. Two lounge chairs are positioned nearby for relaxation.

Home in Germantown

Columbia County Farmhouse with Pool

CarolineRating, 5 stars2 weeks ago

Beautiful house with lots of beds and spaces to hang out. We had a lovely time here visiting the Hudson Valley in the early spring. Would certainly come back!

5 out of 5 average rating, 19 reviews

A spacious outdoor deck surrounds a circular pool, featuring a clear blue surface and a ladder for easy access. A patio umbrella stands over a seating area with two chairs and a table, set against a backdrop of lush greenery and tall trees.

Home in Catskill

NEW! Catskill Family Hideout with Seasonal Pool

DeborahRating, 5 stars1 month ago

What a great spacious home. Plenty of room for the whole family. Clean and neat! Beds were super comfortable! Great water pressure. Beautiful back yard and three season porch. This was our second visit here and it was just as great as the first!!

4.88 out of 5 average rating, 80 reviews

An indoor heated swimming pool is featured, surrounded by wooden paneling and illuminated by colorful LED lights. A hot tub is positioned beside the pool, with two lounge chairs placed nearby. Large windows offer views of the exterior while maintaining a cozy atmosphere.

Home in Newburgh

Entire Home (private pool), Event Friendly

ChannyRating, 5 stars1 week ago

Faisal was extremely responsive throughout our stay. we loved the indoor pool and the game tables. there was a nice selection. The rooms were nice. It was great that the bedrooms were on the same floor as the living room, dining room and kitchen. We came with an elderly person and they were able to make their way around the house. my son asked if he can use the fire pit out in back and he was able to. he collected wood from the side of the house. nice location. we really enjoyed our stay.

4.87 out of 5 average rating, 46 reviews

A spacious backyard surrounds an inground swimming pool, with lounge chairs positioned nearby. Lush greenery and trees create a private atmosphere, while a blooming hydrangea bush adds a touch of color. A shaded area is provided by an umbrella over some seating.

Home in West Hurley

Hudson Valley Oasis with in-ground pool.

WedrichRating, 5 stars5 months ago

Gary and Isabelle were wonderful hosts and communicated very well and were very gracious and helpful throughout our stay. Their home is very cozy and warm and comfortable, we had a wonderful time and had everything we needed there for a great stay.!! I would highly recommend their home for a stay in the Catskills if you are looking for a place there! We’ll definitely be back there in the summer as they have a wonderful large pool in the yard to enjoy !!

4.93 out of 5 average rating, 133 reviews

Home in New Paltz

Harrison Field Pool 10Acres BikeRailTrail 2Town

AlannaRating, 5 stars6 months ago

We had a great weekend celebrating our parents anniversary. The house was plenty big for all of us and the grounds are beautiful. Nathan was quick to respond when we had trouble navigating the AC and made sure we enjoyed our stay!

4.9 out of 5 average rating, 20 reviews

A large country estate is presented, featuring an orange exterior surrounded by lush greenery. The home includes a spacious front entryway with steps leading to double doors, while an expansive driveway and two-car garage are visible on the right.

Home in East Chatham

10 Acre Country Estate with Pool, Hot Tub & Views!

DeborahRating, 5 stars1 month ago

We loved staying here with our family. It worked out perfectly having our daughter’s family on the one side of the house so if the baby cried it wouldn’t wake anyone up. A pack and play was also provided by Justin so we had a place for the baby downstairs as well. The house was roomy and comfortable for everyone. The hot tub wasn’t working right away but they let us know and had it fixed so we were able to use it during our trip. We would definitely stay here again and try it in warmer weather so we could use the pool as well. Thank you for a wonderful place to stay

4.86 out of 5 average rating, 86 reviews

A spacious heated pool, surrounded by a stone deck, sits within a glass-enclosed area with retractable sides. Colorful lounge chairs are positioned around the pool, inviting relaxation. A hot tub can be seen in the background, all amidst a lush landscape of trees.

Home in Saugerties

Unique Contemporary on 40 Pvt Ac, Enclosed Hot Tub

NadineRating, 5 stars2 months ago

Such a great experience that reaffirms how hard hosts work! Robyn communicated the weather problems in advance and let us know things might be iffy getting in because of a winter storm. Instead of just making sure the home itself was pristine, relaxing, and totally picturesque, she made sure our arrival was perfect. Snow plowed, everything iced, bag of goodies hung up on our arrival. It was such incredible, flexible caretaking of the property and the guests! Besides that, onto the regular stuff- awesome kitchen, hot tub, bedrooms, everything super clean. Was a perfect winter stay!

Home in Preston-Potter Hollow

4.91 out of 5 average rating, 32 reviews

Catskill Home w/ Sauna, by ski &Mountain view

DavidRating, 5 stars3 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!

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Condo rentals with a pool

4.87 out of 5 average rating, 86 reviews

An outdoor swimming pool is surrounded by a chain-link fence, featuring clear blue water and several white lounge chairs positioned beside the pool. Lush green grass and trees frame the area, with a view of a red building in the background.

Condo in Hunter

Cozy Gem with Mountain Views

VESNARating, 5 stars1 month ago

Super cozy and lovely home. Very well stocked and closed to everything. Would stay again!

An outdoor swimming pool is surrounded by a secure fence and shaded by tall trees. Several lounge chairs are positioned around the pool area, and blue umbrellas provide shade. Clear blue water reflects the sky above, inviting relaxation.

4.67 out of 5 average rating, 117 reviews

Windham Condo

AlisonRating, 5 stars6 months ago

We had an amazing stay at Kristen’s condo with our family—my husband, our toddler, and our dog. The location was perfect—secluded and peaceful, but still close to hiking trails and charming small towns. The condo was cozy, clean, and well-equipped with everything we needed for a relaxing weekend. Kristen was responsive and helpful, making our stay even better. Highly recommend for a family getaway!

An outdoor heated pool is surrounded by a spacious patio, with two hot tubs nearby. Lush greenery and vibrant autumn foliage create a scenic backdrop. Multiple lounge chairs are positioned along the poolside, inviting relaxation in a serene setting.

5 out of 5 average rating, 21 reviews

Luxury. 5-Star. Ski In/Out, Heated Pool, Hot Tub

JaneRating, 5 stars4 months ago

I had an amazing stay! The home was spotlessly clean, beautifully furnished, and fully stocked with everything I needed for a comfortable stay. It was the perfect place to relax and unwind—definitely a gem!

A cozy living area features a light-colored sofa facing a decorative coffee table. A round rug with a nature motif complements the hardwood flooring. Large windows provide access to natural light, and a balcony can be glimpsed through the sliding glass door.

4.88 out of 5 average rating, 191 reviews

Cozy Mountain hideaway Windham, Hunter

RandolphRating, 5 stars2 weeks ago

Pristine clean, cozy, one bedroom condo unit located in Windham with seasonal access to tennis courts and a pool. Walking distance to the beautiful Windham Path. Slept better than at home in the comfy bed. Went for two days of midweek remote work. Agnieszka, the host, was gracious and responsive. The host obviously put some genuine TLC into this place and it shows. Browsed for books at Briars & Brambles, an indie bookstore in Windham adjacent to Windham Pharmacy. Purchased groceries and firewood down the road at Hickory Hill Market . Ate in area at Higher Grounds and Windham Diner. Living room has a fireplace with large screen TV just above. Great for all seasons. Thanks Agnieszka!

A welcoming living area features a brown leather sofa with decorative pillows, a wooden coffee table, and a comfortable armchair. Soft lighting is provided by a floor lamp and a wall-mounted lamp. A sliding glass door leads to an outdoor deck surrounded by trees.

4.83 out of 5 average rating, 12 reviews

Windham-Hunter Lodge

MariaRating, 5 stars3 months ago

Cullen was an exceptional host. The space was exactly as described, with plenty of supplies. Communication was stellar. The condo had plenty of extras like clean linens and blankets, there were even additional chargers set up and toiletries if we needed. The beds are comfortable. The bathrooms very clean and updated. Parking right in front. We felt safe and comfortable. This AirBnB is 5 minutes to Windham mountain and minutes from Town. Plenty of places to eat and shop. I highly recommend this Host and property. If we ever go back, we will try to re-book with Cullen.

An indoor pool area is showcased, featuring a large swimming pool with clear blue water. Sunlight filters through multiple windows, illuminating the space. Wooden beams and a high ceiling create a spacious atmosphere, complemented by seating options along the poolside.

4.92 out of 5 average rating, 59 reviews

4 Bedroom Condo, Close to Golf Courses and Biking

DianeRating, 5 stars17 months ago

Fit our needs for attending a weekend wedding in the area. Appreciated the 3 full bathrooms. Hosts were very responsive when entry code didn’t work and in providing 2 missing items right away. Wish it was warm enough outside to enjoy the large deck but it was November. Enjoyed our stay.

An outdoor area is shown featuring a heated swimming pool and two hot tubs surrounded by lounge chairs. The space is bordered by a landscaped lawn with neatly arranged trees and mountains visible in the background, creating a serene environment.

5 out of 5 average rating, 5 reviews

Luxury Ski in Ski out Condo + Amenities

AaronRating, 5 stars3 months ago

We worked through a bit of calendar scheduling snafu quickly. Scott was accommodating, proactive, and responsive. The condo was in a great location, maintained well, and clean. We very much enjoyed our quick weekend getaway. Thank you!