Vacation rentals with a pool in Esopus Creek

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Top-rated rentals with a pool in Esopus Creek

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite
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, 189 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

Top guest favorite
A stand-alone guest house is framed by lush greenery, featuring a prominent wall of glass that allows abundant natural light. The exterior is finished in wooden planks, complemented by neatly landscaped flowerbeds at the base.
Cottage in Bearsville
4.96 out of 5 average rating, 135 reviews

Contemporary Guesthouse with Views and Privacy

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.

Guest favorite
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
4.97 out of 5 average rating, 159 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.

Top guest favorite
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
5 out of 5 average rating, 165 reviews

Upstate Modern Scandinavian Barn in the Catskills

Renovated 1850's barn with 3 bedrooms and an ample loft space that can serve as a fourth. The house also has a large rec room with cathedral ceiling buttressed by hand-hewn beams, well-equipped kitchen, Scandinavian wood stove, sauna, home gym, and projector. Outside: 2 private decks with amazing views of Overlook Mountain, private grill, private hot tub. On property: shared tennis court, swing set, fishing pond, heated pool (summer only). 2 hours from NYC, 10 min. to Woodstock & Saugerties.

Guest favorite
A modern living area features large glass doors overlooking a lush green landscape. Natural light fills the space, highlighting the minimalist furnishings, including a stylish sectional sofa and a glass coffee table. Shelving along the wall displays books and decorative items.
Home in Woodstock
4.97 out of 5 average rating, 175 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..

Top guest favorite
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
4.96 out of 5 average rating, 297 reviews

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

Enjoy the serenity of this contemporary home on six private acres central to all the Hudson Valley has to offer; just 20 min. from the NYS Thruway. Year-round hot tub, seasonal salt water pool, fireplace, gourmet kitchen, and large deck & patio w/ fire pit make this the ultimate getaway. Sports enthusiasts, shoppers, and diners will delight in how close we are to amazing Catskills attractions. New Paltz, Kingston, Mohonk Preserve and Minnewaska State Park are just 15 minutes away.

Guest favorite
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
4.89 out of 5 average rating, 133 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

Guest favorite
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
4.95 out of 5 average rating, 392 reviews

Fenced & Salt Water Pool | Cozy Catskills Cottage

The perfect spot to unwind with family, friends, and pups. Spend the day hiking, visiting farms, or trying local restaurants, then come home to the yard for kid-and-dog frolicking, “Squirrel TV” through long windows. Soak in the claw-foot tub or the jetted spa tub, then gather by the fire with wine and board games. Swim and make s’mores in summer, watch snow fall in winter, and enjoy peaceful views in every season, relax, play, laugh, repeat.

Guest favorite
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
4.87 out of 5 average rating, 146 reviews

Gorgeous Villa MntnViews, nr SKI, firepl, hot tub!

Our beautiful Villa has amazing mountain views, a clean, modern design and is the perfect getaway to socialize & relax. It is ideally located for hiking & has a gorgeous, private salt water pool (mid May- mid Oct) and a wonderful hot tub which is open year round! In addition to the main house there is also a spacious studio cottage (with bathroom) & heat that can be used as a WFH private office. It has it's own high speed internet.

Top guest favorite
A bright living area features large windows that invite natural light. A circular rug provides a soft contrast to the wooden flooring, and a modern sectional sofa is accompanied by two armchairs. A decorative mirror and artwork enhance the elegant ambiance.
Home in Kingston
5 out of 5 average rating, 120 reviews

Luxury Retreat with pool in historic Kingston

This historical brick building turned into a private residence on the Hudson River is your luxury retreat with top-notch amenities and finishes; perfect for a getaway weekend and longer stay. The house is 7 min walk from the marina and restaurants in the historic district of Kingston and seconds from the Hudson River. Perfect location for hiking lovers, boat lovers, and nature lovers.

Guest favorite
A spacious living area features a hand-built stone fireplace adorned with decorative elements. Large windows allow natural light to fill the room, which includes a dining space with a long table set for guests. Comfortable seating is positioned around the fireplace on a well-defined area rug.
Home in Saugerties
4.95 out of 5 average rating, 110 reviews

MODERN FARMHOUSE in the WOODS

MODERN FARMHOUSE in the WOODS. 3 Bdr., 2 Bath. Very convenient to Saugerties and Woodstock. New 18' x 36' pool (Open Memorial Day through mid-September). Gourmet kitchen, hand-built stone fireplace, Child friendly. 3 beautiful acres, woods, and a big yard for grilling & fun. Swing set for the kids, stone fire pit for everyone! Washer & Dryer available for stays of 3+ days.

Top guest favorite
A modern cabin stands against a backdrop of lush greenery and mountains. Large windows invite natural light, while a deck with seating is visible in the foreground. Surrounding landscaping includes trees and shrubs, creating a serene and private outdoor space.
Cabin in Arkville
4.97 out of 5 average rating, 155 reviews

Ski & Sauna! Modern Mountain Escape

Welcome to a brand new Catskills getaway. Inspired by Japanese and Scandinavian design, every detail has been thought through to create the perfect private retreat where interiors blend seamlessly with the surrounding mountains. You’ll see high end finishes throughout the space and all the amenities you could desire. Welcome to a relaxing stay at your home away from home.

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