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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.

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Top guest favorite

Home in New Paltz

4.98 out of 5 average rating, 489 reviews

midcentury mod * POOL * walk out trail to mohonk

A Frank Lloyd Wright inspired Mid Century Mod w updated amenities, comfy, clean, open concept. Large windows offer big views of flora/fauna and the many birds & wildlife. Mtn views including skytop. short wooded trail just behind house to access Wallkill Valley Rail Trail, from here walk a scenic mile to R2R trail (take to mohonk) Water St. mkt & the ❤️ of New Paltz Village Several outdoor seating areas. THE WHOLE PLACE IS YOURS FULL PRIVATE ACCESS HOUSE, POOL & PROPERTY POOL OPEN 5/1 - 9/30

A tranquil brook flows through a rocky gorge, surrounded by lush trees and rugged stone formations. The scene showcases the natural landscape, leading toward a wooden deck with a canopy, providing a peaceful retreat in a serene setting.

Home in Rhinebeck

4.89 out of 5 average rating, 141 reviews

4Br Mountain Brook House on 130 acres w/ trails

Hemlock House is an extraordinary private escape nestled against a babbling brook running through the rocky gorge of an 130 acre magical historic farm. Explore hiking trails through old forests, trout creeks, and 90ft waterfall or simply relax by the fire pit or within the outdoor spa while listening to the flowing water. Visit this beautifully designed retreat, complete with gourmet kitchen, cozy fireplace, great wifi and comfortable bedrooms with quiet workspaces- learn more at cascadafarm.com

A sparkling heated pool is framed by natural surroundings, with a stand-alone guest house visible in the background. Lush trees create a serene atmosphere, enhancing the privacy of the outdoor space. Nearby, seating areas and open grass provide inviting spots for relaxation.

Cottage in Bearsville

4.96 out of 5 average rating, 120 reviews

Contemporary Guesthouse with Private Heated Pool

Secluded studio on 13 acres in Bearsville with views of meadows, mountains and woods. Stand-alone guest house with queen size sleeping loft, kitchenette, fully tiled bathroom, elliptical trainer, and all amenities. Wake up in the morning and enjoy the amazing views with your coffee, hike in the woods, or meditate at the waterfall. In season enjoy the completely private heated pool. End the day with s'mores around the fire pit. An ideal getaway from the city yet only three miles to Woodstock.

A spacious living area features two modern armchairs with orange accent pillows facing a large picture window. The serene view of the wooded area surrounding the private pond is visible, inviting natural light into the space. A low coffee table occupies the center, complemented by a soft sofa nearby.

Cottage in Saugerties

4.99 out of 5 average rating, 137 reviews

Black Ridge Cottage: Pond, Cowboy Pool & Sauna

Kick back and relax in this calm, stylish space, with private wildlife filled pond & cowboy pool This house is great for a family, or two couples. There are lots of relaxing spaces inside and several seating areas in nature outside. Ten minutes to the towns of Woodstock and Saugerties, you will have the perfect location to enjoy the best experiences the Hudson Valley has to offer. This 4 bedroom, 3 bath house has been recently gut renovated. Enjoy the beautiful design and natural landscape.

A heated saltwater pool is set within a gated bluestone patio, surrounded by lush greenery. The clear blue water reflects sunlight, creating a serene atmosphere. The pool area is framed by a mature tree line, providing privacy and a peaceful outdoor space.

Cottage in Kingston

4.92 out of 5 average rating, 376 reviews

Kapitan’s Cottage: Private Retreat with Salt Pool

A vintage rustic country retreat with two floors with modern amenities. 2BR, full & half bathroom. Family & Pet friendly. Large yard surrounded by a mature tree line for secluded privacy. Private stone deck w/ fire pit, BBQ & comfortable deck furniture. Summer Pool access and Generator on site. Close to Kingston, High Falls, Stone Ridge and Woodstock yet just far enough out to feel you're away from city hustle and bustle. Close to miles of hiking, outdoor activities, parks & Ski slopes.

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.

Condo in Windham

4.89 out of 5 average rating, 193 reviews

Cozy Hideaway Windham, Hunter ,Pool,Pickleball.

Spacious 1BR condo for a max. of 4 guests , sleeps 2 in separate bedroom , additional 2 on an inflatable airbed . Balcony with mountain view ,2 tennis courts ,outdoor pool . Awesome location . Windham and Hunter within reach .Get close to nature in the nearby hiking trails, Windham Path, Kaaterskill Falls. Kayaking on North-South Lake or ziplining in Hunter,skiing ,snowboarding ,golfing and mountain biking . Leave your worries at home and come to relax.Enjoy many dining options in town.

Home in Kingston

4.85 out of 5 average rating, 104 reviews

Hudson River views with pool and hot tub

The Riverview Terrace House is located in a quiet neighborhood in Kingston NY overlooking the beautiful Hudson River. Just an hour and forty five minutes from NYC it is the perfect get away for family and friends. We welcome you to enjoy the house with 5 bedrooms, 2.5 baths, a pool open during summer months thru Labor Day and a hot tub open year round. Centrally located between uptown Kingston and Rhinebeck you will have access to the all of the great amenities the area has to offer.

Home in Woodstock

4.98 out of 5 average rating, 146 reviews

Woodstock Historic Artist Estate- The Museum House

The property is an estate formerly owned by renowned artist Reginald Marsh located within a 10 minute walking distance to the center of the historic town of Woodstock, NY. The 2500sft house is the former Museum House that used to hold Mabel Marsh’s art collection that was later acquired by the Smithsonian Institute. It has been architect gut-renovated into a dramatic living experience surrounded by nature and water. The Pond and Carriage House are at the opposite side of the estate..

4.91 out of 5 average rating, 117 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. Ok

Top guest favorite

A circular above-ground pool is surrounded by lush greenery and trees. The water's surface reflects the clear blue sky, creating a serene atmosphere. Sunlight filters through the leaves, casting gentle light on the poolside.

Apartment in New Paltz

4.93 out of 5 average rating, 331 reviews

Peaceful and Private Boutique Apartment *Pool*

Welcome to your serene retreat one mile from charming downtown New Paltz! Our pretty boutique apartment offers a peaceful escape, perfect for couples or families. Enjoy the comfort of a private entrance, luxurious king and queen beds, kitchen, stocked coffee bar, and huge yard. End your day with a refreshing dip in our pool or unwind in the hammock. Just minutes from town and hiking trails, and many local activities. Experience the best of New Paltz – book your stay today!

A swimming pool is featured, surrounded by a wooden deck and a fence. Two individuals are seen enjoying the water, while a dog observes from the edge. Several lounge chairs are arranged nearby, with greenery visible in the background.

Cottage in Rhinebeck

4.88 out of 5 average rating, 184 reviews

Secluded peaceful loft in barn by woods

La Barn Bleue sits on top of a hill by a forest, in a secluded and peaceful property. The main house, where we live is 150 feet down the hill. The apartment sleeps up to 4 people. The bedroom/lounge loft has one king bed and 2 twin beds. Ideal for families and kids above 5 years old. Because we use a rope railing, we cannot host kids under 5 years old for security reasons. We offer Wifi, AC/heat split unit, outdoor Picnic table, bbq, petanque court and pool!

A wooden deck is shown, featuring a set of stairs leading up to a fenced area. The gray wood contrasts with the surrounding trees, indicating a natural and serene setting. Bare branches suggest winter, while leaves lay scattered on the wooden surface.

Guest suite in Saugerties

4.93 out of 5 average rating, 141 reviews

Tyrolean Style Country House in Saugerties, NY

Tyrolean style, two family house on two acres, (owner and family are onsite and lives in the bottom unit) fully furnished 3 bed, 2 bath home, fireplace. AC in master and living room only. WIFI throughout. Guests have separate parking, entrance, back deck with a big table & 8 chairs. The house is newly renovated, new luxurious bedding in each bedroom. Wake up surrounded by trees and to a beautiful sunrise. Perfect for a romantic weekend or family vacation.

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Popular amenities for Ulster rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

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, 179 reviews

Private Hudson Valley Country Retreat

MarkRating, 5 stars6 months ago

Place was perfect! Clean & made our Holiday stay in the beautiful Hudson Valley a wonderful experience. We loved the personal touches the house offered and we will be back

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.

An aerial view captures the lush green landscape surrounding the property, highlighting a swim pond at the center, framed by natural stones. Scenic mountains rise in the background, offering a serene backdrop, while trees provide shade around the area. Hanging swing chairs are visible nearby.

Home in Saugerties

4.88 out of 5 average rating, 132 reviews

Shaggerties - fun cozy catskill mountain getaway

OhadRating, 5 stars2 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.

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.

4.96 out of 5 average rating, 156 reviews

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

ChristopherRating, 5 stars2 weeks ago

Very enjoyable time here! Instructions, accommodations, and overall experience was perfect!

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

4.87 out of 5 average rating, 134 reviews

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

JenaRating, 5 stars1 month ago

Beautiful view, great space for our girls weekend trip!

An open living space is visible, featuring wooden beams that create a warm atmosphere. The dining area is filled with natural light, showcasing a wooden table surrounded by chairs, with modern light fixtures above. A staircase leads to the upper floor, enhancing the spacious design.

Home in New Paltz

4.86 out of 5 average rating, 159 reviews

Scenic River View Escape | New Paltz

TatiaRating, 5 stars2 weeks ago

I spent my birthday at this beautiful house and couldn’t have asked for a better experience. The place was spotless and full of natural light, with lovely views that made the stay even more special. The atmosphere was peaceful and clean, and the house had everything we needed for cooking and relaxing. I truly felt at home and appreciated all the thoughtful touches. Highly recommend for anyone looking for a cozy, well-equipped getaway!

Home in New Paltz

4.93 out of 5 average rating, 135 reviews

Harrison Field June11-16 LastMinuteWeekend GetAway

EmmaRating, 5 stars2 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!

Top guest favorite

A spacious deck features two comfortable chairs and a round table at its center, offering a clear view of the expansive Catskill Mountain landscape. Lush greenery and rolling hills stretch into the distance under a bright blue sky.

Home in Stamford

4.98 out of 5 average rating, 113 reviews

Hawk View

ZacharyRating, 5 stars2 weeks ago

The house is really gorgeous. Everything was very new/modern, clean, and comfortable. We enjoyed cooking meals in the kitchen overlooking the stunning view out the back. The hot tub and fire put were nice amenities to enjoy. The BBQ seemed to not be working, but other than that, no complaints. Location wise, the property is located in the northwest Catskills, near Stamford, NY, and convenient to many hiking spots in the area as well as nearby towns. The property itself its up on a hill, in what felt like a secluded and private spot, which made it feel like a real getaway and retreat. In sum, recommend this Airbnb for the nice amenities, modern touches, and amazing view.

Condo rentals with a pool

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 stars2 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.

A spacious living area features an arrangement of dark leather seating and a wooden dining table. Natural light streams through sliding glass doors that open to a balcony. A stone fireplace adds character, while decorative plants and artwork enhance the inviting ambiance.

Condo in Hancock

4.95 out of 5 average rating, 58 reviews

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

EladRating, 5 stars1 month ago

A Perfect Stay at Elisa's! Elisa's place was absolutely magical! Located in a charming yet convenient resort, this beautifully designed space instantly felt like home. Sunlight streams through the windows, illuminating tasteful décor that balances style and comfort. What truly stands out is Elisa's hospitality. Her communication was warm and helpful, and her local recommendations led us to hidden gems throughout the area. The spotless cleanliness and private garden oasis for morning coffee or evening drinks made everything perfect. This place represents exceptional value—not just accommodation but an experience connecting you to the local community.

An outdoor pool is visible, surrounded by lounge chairs and shaded by umbrellas. Lush greenery and trees provide a natural backdrop, with a resort building in the distance. Clear blue skies add to the inviting atmosphere of the space.

Condo in New Ashford

5 out of 5 average rating, 5 reviews

Wyndham Bentley Brook - 2 BR Deluxe - Sleeps 8

MichelleRating, 5 stars3 months ago

Great stay! Listing as described. My family really enjoyed our stay.

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 stars3 weeks ago

Was as advertised. Would recommend

Icicles hang from a structure in the foreground, with a view of snow-covered ski slopes illuminated by soft lights in the distance. The landscape is blanketed in fresh snow, creating a serene winter atmosphere.

Condo in Hancock

5 out of 5 average rating, 4 reviews

Wyndham Bentley Brook

Ashley And NathanielRating, 5 stars15 months ago

We had a wonderful time staying at Paul’s place! We had easy access to the mountain for skiing. It was wonderful to have a ski locked to store our stuff outside of the room. In addition to the wonderful accommodation our kids loved the indoor/outdoor pool after a long day on the slopes. Highly recommend Paul and his accommodation!!!

A living area features a beige sofa with cushions, positioned beside a dark wood coffee table. Natural light enters through a large window with tan drapes, offering a view of grassy landscaping. A simple lamp stands next to the sofa, enhancing the cozy ambiance.

Condo in Hancock

4.92 out of 5 average rating, 65 reviews

Jiminy Peak Country Inn - ski in/out condo MT view

MeganRating, 5 stars1 month ago

Very nice spot for one person or a couple. Convenient access to JP base area and amenities. Neat and tidy space, nicely appointed. Great communication from owner.

A clear swimming pool is enclosed by a fence, featuring a ladder for easy access. Lush greenery and the mountains are visible in the background, with lounge chairs positioned nearby. The scene is set under a bright blue sky with wispy clouds.

Condo in East Jewett

4.97 out of 5 average rating, 124 reviews

MountainViewBrightCondo10MinToColgateLakePool

JudithRating, 5 stars3 weeks ago

We booked the place for a family stay near Woodstock. It was easy to get in. There’s automated messages for every step of the stay with instructions which was very nice and helpful. We had a great stay in a worm and clean space. Would definitely go back.

A serene view of well-maintained landscaping surrounding a tranquil pond is presented. The image captures multiple condo buildings set against a clear blue sky with scattered clouds. Lush green grass leads to the water's edge, framed by several mature trees.

4.8 out of 5 average rating, 10 reviews

Tranquil Lakeside Escape in the Berkshires

GregoryRating, 5 stars2 weeks ago

Beautiful property. We enjoyed very much the tranquility. There was an issue with the kitchen light but maintenance was going to address it. The exterior of some of the buildings needs to be worked on, but overall the place was great.

Quick stats about vacation rentals with a pool in Ulster

Total rentals
30 properties
Nightly prices starting at
ﺩ.ﺇ404 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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