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Vacation rentals with a pool in Ulster

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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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Guest favourite
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

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

4.88 out of 5 average rating, 220 reviews
Guest favourite
A striking landscape features a modern home beside a serene pond. Lush green lawns and colorful trees reflect beautifully in the water. Towering conifers and deciduous trees frame the scene, enhancing the idyllic outdoor setting.
Home in Woodstock

Woodstock Historic Artist Estate - The Pond House

Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

4.94 out of 5 average rating, 398 reviews
Superhost
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 Indoor Pool

This unique specious and tranquil getaway private home includes an indoor heated swimming pool, hot tub, an outdoor space of 34 acres for you to enjoy nature, work out equipment, movie theater. Complete eat in kitchen, outdoor grill. washer and dryer, three bathrooms. Huge open space basement equipped with LED changing color light. Rooms have Wi-Fi LED light to connect music. The place sleeps 8 guests, in beds. Two additional twin mattresses.16 guests maximum. Hot tub take a while to heat up.

4.81 out of 5 average rating, 136 reviews
Top guest favourite
A comfortable living room is highlighted by warm-toned walls and polished wood floors. A sectional sofa offers spacious seating, complemented by a rustic coffee table. A brick fireplace adds character, while natural light filters through white curtains on multiple windows.
Home in Saugerties

Viewtop Farmhouse-Fall in the Hudson Valley

Enjoy View Top Farm House, a rustic, 100+ yr old, farmhouse/former boarding house on 3 beautiful acres, overlooking the Catskill mountains. Enjoy time on the patio by the fire, barbecuing, eating alfresco or swinging in the hammock. Its 15 min to the Rondout, 7 min to the Village of Saugerties. Get breakfast, lunch or dinner out, or cook at home in the large, well stocked kitchen. Minutes from restaurants, antique stores, hiking, and biking. Enjoy many amenities. Well behaved pets are welcome.

4.94 out of 5 average rating, 139 reviews
Top guest favourite
Home in High Falls

Comfortable & Spacious Country Home - All Seasons

We welcome you to stay at our inviting home in the hamlet of High Falls. The two-story early 1900's era farmhouse is set on 12 private acres off a quiet country road in a lovely residential area. Grounds feature access to woods, pond and canoe-ready Roundout Creek. A large sunlit family room, a variety of games, vast outdoor space with furnished patio, in-ground pool/deck/BBQ/swings/firepit/hammock offer the perfect place to relax and restore your connection to nature, friends and family.

4.98 out of 5 average rating, 121 reviews
Top guest favourite
An aerial view captures The Evergreen retreat set on three acres, showcasing a spacious yard surrounded by trees. A heated pool is visible beside a patio area with a dining table, while a fire pit is centrally located, enhancing the outdoor experience.
Home in Saugerties

Woodstock Getaway - Heated Pool/Hot Tub/FirePit

Welcome to The Evergreen, our Catskills retreat located 5 minutes from Woodstock village. Sitting on 3 acres amongst the trees, this property boasts beautiful outdoor space with a heated pool*, hot tub, outdoor dining area, grill, and a fire pit, creating the perfect setting for relaxation and entertainment. This charming property offers 5 bedrooms & 3 full bathrooms, perfect for large families or groups of friends. It also features a study, ideal for those who need to balance work and play.

4.98 out of 5 average rating, 128 reviews
Superhost
The exterior of the house showcases a combination of stone and brick, framed by well-kept landscaping. A mature tree offers shade in the front yard, while a pathway leads to the entrance. The roof features a peak with multiple gables.
Home in Kingston

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.

4.79 out of 5 average rating, 132 reviews
Guest favourite
An aerial view showcases the spacious home surrounded by trees and a manicured lawn. Outdoor seating is featured on the deck, illuminated by string lights. A fire pit area is visible, enhancing the outdoor gathering space for relaxation and socializing.
Chalet in Ruby

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

4.9 out of 5 average rating, 140 reviews
Top guest favourite
A spacious country house is showcased with a large wraparound deck featuring an umbrella and seating. The well-maintained grounds include greenery and a glimpse of an above-ground pool in the background, complemented by a clear blue sky.
Home in Saugerties

Peaceful Hudson Valley Getaway

Best for families! Relaxing and playful retreat! Come for the hiking, antiquing, HITS shows, farmer's markets, visits to Bard College! Especially KID FRIENDLY with all the necessary amenities. Enjoy the pool, deck, gas grill, fully stocked kitchen, bikes, hammock, fire pit, and open floor plan for gathering and home cooked meals. Feel free to message me if you are looking for specific dates that are marked unavailable. From June - August, 3 night minimum.

4.93 out of 5 average rating, 127 reviews
Guest favourite
Cabin in Kingston

Modern Getaway in Kingston - 1.5hr from NYC

Split-level 5 bd 3 ba home with a private pool, BBQ grill and fire pit. We have a fully stocked kitchen, children's items & are just 5 minutes from town. We‘re looking to share our home as a peaceful retreat with families and quiet groups only as we have neighbors close by. This is our personal home and we have a no-shoe policy. We kindly ask that you pass on this house if you are not comfortable with this. 1 pet under 35 lbs allowed with a pet fee.

4.91 out of 5 average rating, 117 reviews
Top guest favourite
A two-story house stands on a gently sloping hill, surrounded by lush green grass. The property features a large, covered porch that wraps around part of the home, offering views of the expansive yard and surrounding trees.
Home in Tivoli

Upstate Getaway btw Rhinebeck+Hudson

Our home is located on an unpaved, private road in a quiet area and features an in-ground, heated, saltwater pool open between Memorial Day and Late September. In 2026, the pool will be available for bookings 5/22 - 9/18. A quiet and private getaway in the Hudson Valley and convenient to many popular activities. NOTE: For bookings during pool season, guests will be asked to review and agree to the safety rules relating to the pool.

4.98 out of 5 average rating, 102 reviews
Top guest favourite
The spacious bedroom features a large bed with a geometric patterned duvet and plush pillows. Flanking the bed are two nightstands with lamps. A cozy area rug complements the hardwood floor. Robes are hung on the wall, and a doorway leads to the en suite bathroom.
Home in Saugerties

Bluestone Escape - Where everyone is at home.

Bluestone Escape is a thoughtfully curated home designed by NYC interior designer Rhobin DelaCruz. Each decision was carefully made with comfort and style as the foundation of all choices. Bluestone Escape isn't just another rental, it's an experience. From hand picked artwork to the simpler detail of USB enabled outlets, Bluestone Escape will feel like the second home you are glad you have.

4.94 out of 5 average rating, 159 reviews

Popular amenities for Ulster rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Guest favourite
An aerial view captures the red dairy barn, featuring a colorful roof with decorative elements. Surrounding greenery and open fields create a serene backdrop, while a winding path leads to the barn entrance, inviting exploration of the surrounding landscape.
Home in Woodstock

The Woodstock Barn House - Sauna, Gym, Jacuzzi

4.99 out of 5 average rating, 277 reviews
Superhost
A tranquil saltwater pool is set against a natural stone backdrop, surrounded by lush greenery. Poolside, a sunbed and umbrella are positioned, providing a relaxation spot. The patio features a rugged stone surface, enhancing the outdoor experience amidst a serene atmosphere.
Home in Saugerties

Highwoods Haven | saltwater pool and hot tub

4.86 out of 5 average rating, 131 reviews
Top guest favourite
Home in Woodstock

Woodstock Family Home w/ Tree House + Heated Pool

4.97 out of 5 average rating, 129 reviews
Top guest favourite
An aerial view captures the expansive landscape surrounding the barn, featuring vibrant autumn foliage and rolling mountains in the background. A serene pond is nestled among the trees, with the property’s expansive lawn visible in the foreground, emphasizing the natural beauty of the 12-acre site.
Home in Saugerties

Upstate Modern Scandinavian Barn in the Catskills

5.0 out of 5 average rating, 172 reviews
Top guest favourite
Home in Athens

Lake House close to Skiing & Indoor Hot Tub

4.96 out of 5 average rating, 112 reviews
Top guest favourite
A wooden lounge chair is positioned near a serene saltwater pool, surrounded by lush greenery. The pool's clear water reflects the inviting outdoor space, which is complemented by concrete paving and a manicured lawn.
Home in Cottekill

Peace & Privacy - High Falls (hot tub & salt pool)

4.96 out of 5 average rating, 309 reviews
Top guest favourite
Home in Saugerties

Enjoy Pool, Bocce Court, Fire Pit -Close to HITS

5.0 out of 5 average rating, 112 reviews
Guest favourite
A panoramic view of distant mountains stretches under a clear blue sky. The landscape features a mix of trees and open areas, showcasing the natural beauty of the surroundings.
Home in Woodstock

Gorgeous Villa Mntn Views • POOL • hot tub •grill!

4.88 out of 5 average rating, 153 reviews

Condo rentals with a pool

Guest favourite
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

Stunning Views • Bright 2BR • Pool • Near Farm • Lakes • Farm

4.94 out of 5 average rating, 157 reviews
Guest favourite
A cozy bedroom features rustic wooden walls with decorative hearts. A spacious bed is dressed in light linens, accompanied by a bedside lamp and a small dresser. A guitar leans against the wall, adding a touch of character to the room.
Condo in Hunter

Cozy Gem with Mountain Views

4.89 out of 5 average rating, 116 reviews
Superhost
A spacious outdoor deck is visible, furnished with a round table surrounded by several chairs and a lantern on top. A comfortable seating area with a couch is positioned nearby, set against a backdrop of lush greenery.
Condo in Windham

Windham Condo

4.69 out of 5 average rating, 127 reviews
Superhost
Condo in Windham

Cozy Mountain Condo w/ Pool

4.84 out of 5 average rating, 19 reviews
Guest favourite
A bright living area is featured, showcasing a cozy arrangement of gray sofas around a circular coffee table. A modern ceiling fan circulates air above while large windows reveal stunning valley views, allowing natural light to fill the room. An electric fireplace adds warmth to the space.
Condo in Windham

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

5.0 out of 5 average rating, 31 reviews
Guest favourite
Condo in Windham

Hideaway Windham/Hunter Fireplace, Snow & Skiing

4.9 out of 5 average rating, 254 reviews
Guest favourite
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

Windham Mountain Ski In Ski Out - Pool Hot Tub Gym

5.0 out of 5 average rating, 7 reviews
Guest favourite
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

Luxury Ski in Ski out Condo + Amenities

5.0 out of 5 average rating, 11 reviews

Other vacation rentals with a pool

Top guest favourite
A serene meadow unfolds beneath a cloudy sky, with lush green grass leading into a gentle expanse of golden fields. Towering trees line the horizon, creating a natural boundary between the open landscape and the dense wooded area beyond.
Farm stay in Ulster Park

Lovely country house; stunning view

4.91 out of 5 average rating, 174 reviews
Top guest favourite
Farm stay in Saugerties

Catskills Family Retreat: Pool, Sauna and Animals!

4.98 out of 5 average rating, 187 reviews
Guest favourite
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

Black Ridge Cottage: Pond, Cowboy Pool & Sauna

4.97 out of 5 average rating, 172 reviews
Guest favourite
A spacious living area features large windows allowing natural light to flow in, complemented by a sectional sofa and an ottoman. A television is positioned on a media console, and a rug with a geometric pattern enhances the wooden floor.
Guest suite in Saugerties

Tyrolean Style Country House in Saugerties, NY

4.9 out of 5 average rating, 183 reviews
Guest favourite
A charming red cottage is set against a backdrop of lush greenery and blue skies. The landscaped yard features well-maintained grass and a variety of trees, providing a serene outdoor environment. Nearby, an additional outbuilding is visible, enhancing the rustic atmosphere.
Guesthouse in Olivebridge

Sweet Fern Cottage With Saltwater Pool

4.93 out of 5 average rating, 286 reviews
Top guest favourite
A modern cabin features a peaked roof and large glass windows, set amidst lush greenery. A heated pool is visible in the yard, surrounded by comfortable lounge chairs, inviting relaxation in a tranquil outdoor setting.
Cabin in Red Hook

Modern Upstate Cabin, near Rhinebeck NY

4.96 out of 5 average rating, 395 reviews
Top guest favourite
The exterior view of the guest house is framed by a large tree, showcasing the red brick barn-style structure. Outdoor seating areas are visible, along with a shaded patio featuring a red umbrella. The surrounding lawn is well-kept, leading to fenced paddocks in the background.
Farm stay in Red Hook

Sackett & Van Dam Guest House @ Little 9 Farm 1706

4.98 out of 5 average rating, 176 reviews
Top guest favourite
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

Contemporary Guesthouse with Heated Pool

4.97 out of 5 average rating, 148 reviews

Destinations to explore