
Vacation rentals with a pool in Ulster
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Ulster
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Ulster rentals with a pool
House rentals with a pool

Shula | Farmhouse | Pool, Fire pit, Hot tub
Cute house, open concept first floor was great for a weekend with our girlfriends! Hava was very responsive and kind!

Private Hudson Valley Country Retreat
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!

Woodstock Oasis Heated Pool, Deck & Prime Location
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.

Shaggerties - fun cozy catskill mountain getaway
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.

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres
Very enjoyable time here! Instructions, accommodations, and overall experience was perfect!

Modern Barn on 12 acres w Sauna, FirePit+swimming
Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.

Harrison Field Pool Bike2Town FirePit 10AcreViews
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!

Upstate Modern Scandinavian Barn in the Catskills
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

Cozy Gem with Mountain Views
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.

Windham Condo
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!

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

4 Bedroom Condo, Close to Golf Courses and Biking
Very nice place with decent pricing. lots of room, clean, good communication from host.

Windham Mountain Ski In Ski Out - Pool Hot Tub Gym
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.

Luxury Ski in Ski out Condo + Amenities
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!

Summer Retreat w/ Balcony & inground Pool
Was as advertised. Would recommend

Ski Windham Mountain ( Catskills, NY)
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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- Hunter Mountain
- Bethel Woods Center for the Arts
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- The Kartrite Resort & Indoor Waterpark
- John Boyd Thacher State Park
- Albany Center Gallery
- Taconic State Park
- Resorts World Catskills
- Catamount Mountain Ski Resort
- Zoom Flume
- Windham Mountain
- Kent Falls State Park
- Walkway Over the Hudson State Historic Park
- Bash Bish Falls State Park
- Hudson Highlands State Park
- Brotherhood, America's Oldest Winery
- Norman Rockwell Museum
- Beartown State Forest
- Mohawk Mountain Ski Area
- Hancock Shaker Village
- Hunter Mountain Resort
- Opus 40