Vacation rentals with a pool in Ulster

Find and book unique homes with a pool on Airbnb

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Popular amenities for Ulster rentals with a pool

House rentals with a pool

Superhost
An above-ground pool is surrounded by a wooden deck featuring lounge chairs. Lush greenery and trees provide a natural backdrop, while a fenced area with a swing set is visible in the distance, creating a serene outdoor space for relaxation.
Home in Woodstock
4.89 out of 5 average rating, 166 reviews

Shula | Farmhouse | Pool, Fire pit, Hot tub

MimiRating, 5 stars3 weeks ago
Cute house, open concept first floor was great for a weekend with our girlfriends! Hava was very responsive and kind!
Guest favorite
A serene view of a private lake is complemented by a well-maintained pool area. Lounge chairs and umbrellas are arranged around the pool, with lush greenery and trees framing the landscape. The clear water of the lake reflects the surrounding nature under a soft, cloudy sky.
Home in Stormville
4.94 out of 5 average rating, 182 reviews

Private Hudson Valley Country Retreat

JackieRating, 5 stars2 weeks ago
This beautiful property has a special place in our hearts. We stayed in the A frame during COVID and we always wanted to come back. This time we stayed in the main house and it was phenomenal. Wish the weather was better for us to use the pool, but next time! It well worth the price. Only an hr from the city and it feels like a full vacation. Wonderful way to lose time time for a few days. We will be back!
Guest favorite
A heated salt-water pool is surrounded by greenery, with lounge chairs positioned nearby. A bright yellow rubber duck floats on the water, while the pool is bordered by textured pavers. Tall trees provide a natural backdrop, ensuring privacy and tranquil views.
Home in Woodstock
4.86 out of 5 average rating, 213 reviews

Woodstock Oasis Heated Pool, Deck & Prime Location

HeatherRating, 5 stars1 month ago
The house is beautiful and the location was lovely, but there were a few things that fell short of the listing description. There was a strong mildew smell in the garage (even after the handyman aired it out), and some basic amenities were missing, like laundry baskets, food storage space, and charging cords for the speakers. There were also only two tall drinking glasses, which was tricky for a group. The outdoor living area shown in the listing wasn’t set up when we arrived, and we would have loved to enjoy it if the cushions were more accessible. That said, the host was very responsive when we reached out with concerns, which we appreciated. With a few tweaks to better prepare the home for guests, this could be a truly wonderful stay.
Guest favorite
Home in Saugerties
4.88 out of 5 average rating, 132 reviews

Shaggerties - fun cozy catskill mountain getaway

OhadRating, 5 stars3 weeks ago
Awesome property for a weekend getaway from the city. Sonny made this place into a fun playground - the pond is amazing, the hot tub, sauna, and back deck felt like a spa, and we enjoyed the fire pit and taking a short hike to the creek. The house itself is simple but has everything you need and we even managed to order Uber eats once from Kingston. The area is great, and we enjoyed the villages and a nice hike in the area. We will definitely come back.
Guest favorite
A stock tank plunge pool is surrounded by a wooden deck and gravel, featuring a pink flamingo float. A lounge chair rests nearby, inviting relaxation in the natural setting of greenery.
Home in Hudson
4.96 out of 5 average rating, 156 reviews

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

ChristopherRating, 5 stars3 weeks ago
Very enjoyable time here! Instructions, accommodations, and overall experience was perfect!
Guest favorite
The serene swimming pond is framed by lush greenery and vibrant flowers. A wooden deck with lounge chairs overlooks the water, while a gentle slope of open lawn leads to the rustic guest house, partially shaded by trees under a clear blue sky.
Home in Ghent
4.88 out of 5 average rating, 318 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

JasonRating, 5 stars3 weeks ago
Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.
Guest favorite
Home in New Paltz
4.93 out of 5 average rating, 135 reviews

Harrison Field Pool Bike2Town FirePit 10AcreViews

EmmaRating, 5 stars3 weeks ago
We had a great stay at Nathan’s place. The playroom was great for our kids and we all enjoyed the pool. The view was also beautiful. We will definitely be back!
Guest favorite
Home in Saugerties
5 out of 5 average rating, 152 reviews

Upstate Modern Scandinavian Barn in the Catskills

Zoe StarRating, 5 stars3 weeks ago
We truly enjoyed our stay at Wilderkill Barn. Maria Cristina and William were exceptional hosts—warm, attentive, and genuinely committed to making our visit special. They went above and beyond to make us feel welcome. The home was a haven, with a hot tub, sauna, pool, fire pit, pool table, and immersive sound and movie systems—all of which made our stay delightful despite the cold, dreary May weather. We can't thank them enough. ***That said, we feel it's necessary to address a serious issue with Airbnb itself that arose while booking this property, unrelated to the property itself. An unexpected tax was added after booking, and Airbnb has yet to provide a clear explanation. After years of loyalty, we were disappointed by their evasive and unhelpful customer support. This experience has made us reconsider using the platform in the future. We urge potential users to scrutinize all fees carefully and be aware that Airbnb’s support may be difficult to navigate if problems arise.***

Condo rentals with a pool

Guest favorite
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
4.87 out of 5 average rating, 87 reviews

Cozy Gem with Mountain Views

AbishekRating, 5 stars4 weeks ago
Loved this place. Very easy to find. The place is cute and co portable with good views from the main bedroom and living room. Very clean and tidy. Loved the stay.
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.
Condo in Windham
4.67 out of 5 average rating, 117 reviews

Windham Condo

AlisonRating, 5 stars8 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!
A welcoming living area features large glass doors offering views of the outdoors, with natural light enhancing the space. A comfortable seating arrangement includes a dark blue chair and a sectional sofa, while a stylish large area rug adds warmth. Decorative elements include wall art and a blooming floral arrangement.
Condo in East Jewett
4.97 out of 5 average rating, 29 reviews

Hunter & Windham: Hikes, Lakes, Swimming, 2BR

LauraRating, 5 stars8 months ago
My friends and I really enjoyed our stay. We hiked the devils path trail and Dimitry’s place was perfectly close to the trail and the restaurants around it. His place was great to go back to with a great shower and bath, a beautiful view and very cozy place, with coffee and a coffee maker. Very clean and Dimitry was responsive the whole way through and checkin and out was very easy. Would highly recommend and would stay again.
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.
Condo in Windham
4.92 out of 5 average rating, 61 reviews

4 Bedroom Condo, Close to Golf Courses and Biking

BrianRating, 5 stars1 month ago
Very nice place with decent pricing. lots of room, clean, good communication from host.
A spacious living area is highlighted by large windows that provide views of the surrounding landscape. A modern fireplace is set against a stone feature wall, while comfortable seating options include a sectional sofa and accent chairs. A flat-screen TV is mounted above a stylish entertainment unit.
Condo in Windham
5 out of 5 average rating, 3 reviews

Windham Mountain Ski In Ski Out - Pool Hot Tub Gym

SamanthaRating, 5 stars16 months ago
We recently stayed at Andrew's condo, and it was nothing short of amazing! The location couldn't be better – right next to the slopes with easy accessibility to the mountain and the ski rental place. We were a group of two families, totaling 6 kids and 4 adults, and the condo was the perfect accommodation for our ski trip. The kids were thrilled with their bunkbed rooms, each equipped with their own TVs, providing a cozy and entertaining space for them to unwind after a day on the slopes. The condo itself was beautifully decorated, creating a warm and inviting atmosphere. There was plenty of room for all of us to relax and spend quality time together. The highlight for both kids and adults was undoubtedly the hot tub and pool. After a day of skiing, it was pure bliss to soak in the hot tub and enjoy the breathtaking views. A special shoutout to Andrew, our fantastic host! He was incredibly responsive and welcoming, ensuring that our stay was comfortable and stress-free.
Guest favorite
An aerial view captures the Whisper Creek condo set against a snowy mountain backdrop, with ski slopes winding down the hillside. The landscape features a mix of pine trees and winter terrain, while the luxury building connects to the scenic outdoors.
Condo in Windham
5 out of 5 average rating, 5 reviews

Luxury Ski in Ski out Condo + Amenities

AaronRating, 5 stars5 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!
Superhost
The exterior of a two-story, wooden condo is visible, featuring a warm brown facade. A covered entrance with an American flag hangs beside the stairs leads up to the unit. Lush greenery and decorative shrubs enhance the inviting surroundings.
Condo in Windham
4.73 out of 5 average rating, 280 reviews

Summer Retreat w/ Balcony & inground Pool

AndrewRating, 5 stars1 month ago
Was as advertised. Would recommend
A spacious sectional couch, upholstered in dark fabric, is arranged around a glass coffee table. The wall is decorated with three art pieces featuring deer antler silhouettes. Light cream curtains frame a window, and a lamp provides additional lighting in the cozy seating area.
Condo in Windham
4.8 out of 5 average rating, 15 reviews

Ski Windham Mountain ( Catskills, NY)

RichardRating, 5 stars41 months ago
We had a wonderful long ski weekend and thoroughly enjoyed this property. Philip was a wonderful and communicative host and we would absolutely come for a visit again. Highly recommended!

Quick stats about vacation rentals with a pool in Ulster

  • Total rentals

    30 properties

  • Nightly prices starting at

    G$23,026 GYD before taxes and fees

  • Total number of reviews

    2.2K reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

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