Vacation rentals with a pool in Shandaken

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Top-rated rentals with a pool in Shandaken

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Guest favorite

An in-ground pool is situated amidst a lush green landscape, surrounded by tall grass and shrubs. The house, a charming two-story structure, is visible in the background, framed by gentle hills under a pastel sky. Outdoor seating and umbrellas are arranged nearby.

Home in Grahamsville

4.9 out of 5 average rating, 105 reviews

Spacious Catskills Farmhouse on over 5 acres!

Come take a dip in our 8' deep in-ground pool and enjoy summer in the Catskills! There is so much to do here! Relax at a spa, try your luck at the casino, go for a hike, or shop at a local Farmer's Market. Enjoy our grounds with a hike on the property, a BBQ in the backyard, or roast marshmallows by the firepit. You will feel right at home in this charming & restored 5BR farmhouse. Located on 5+ acres near the great Catskills Forest Preserve, this is a great place for four season recreation.

Top guest favorite

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, 130 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.

Top guest favorite

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

4.93 out of 5 average rating, 391 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.

Top guest favorite

The outdoor area features a clear saltwater swimming pool, surrounded by lush greenery and well-maintained grass. A wooden structure is visible in the background, partially shaded by trees, creating a serene atmosphere. The pool's surface reflects natural sunlight, creating a calming ambiance.

Chalet in Mount Tremper

4.98 out of 5 average rating, 153 reviews

Secluded Woodstock Retreat with Pool and Sauna

Stunning, tranquil mountainside retreat with exposed beams, saltwater swimming pool, sauna, fireplace, soaking tubs and rain shower. Situated on a 5-acre wooded hilltop a ten minute drive from Woodstock and close to miles of walking trails. Roast marshmallows on the fire pit, flip burgers on the top of the line charcoal grill, and enjoy one of the best stargazing spots around. Indoors, find a well equipped kitchen and cinema sized tv screen with Netflix/Apple TV. Convenient to ski slopes.

Guest favorite

The outdoor space is illuminated by string lights, creating a serene ambiance at night. A pool reflects the soft glow of surrounding lights, while comfortable seating and a hot tub are positioned nearby, nestled among lush greenery and wooden decking.

Chalet in Olivebridge

4.99 out of 5 average rating, 166 reviews

Spruced Moose Lodge w. Hot Tub & open Pool to oct

*Pool Open Until Oct 21!* Secluded log home nestled in 5 acres of Catskill mountain forest, with 4 bedrooms & 3.5 baths (incl. basement with built-in full size bunks). Enjoy a sunroom, screened porch, pool+ brand new hot tub, projection screen home theater & a treehouse that resembles a floating pirate ship 30 feet up in the trees. We renovated the kitchen & master bed with new walls of windows in May - pics to come! Town of Olive Registration No: STR-23-2 SEC-BLK-LOT: 52.4-1-5.500

Guest favorite

Cabin in Shandaken

4.96 out of 5 average rating, 211 reviews

Camp Catskills: Heated Pool Open Through Sept

7 min drive to Phoenicia 10 min drive to Belleayre 25 min drive to Hunter 35 min drive to Windham Renovated 1920’s cabin style home nestled on 4 acres in the Catskill Mountains. Easy to get to and conveniently located near great restaurants, skiing, hiking, tubing, fishing, and swimming holes. A ton of outdoor space to enjoy in addition to our fully private seasonal pool (Late May-Sept). 6 person hot tub is available year round. Not for parties!! Please be mindful of our neighbors!

Guest favorite

Home in Woodstock

4.97 out of 5 average rating, 157 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..

Superhost

A serene salt-water pool is set within a wooded environment, surrounded by lush greenery. Wooden steps lead down to the pool area, which features lounge chairs positioned for relaxation and enjoyment. Sunlight reflects off the water, enhancing the inviting atmosphere.

Cabin in Kerhonkson

4.82 out of 5 average rating, 254 reviews

Secluded Home: Pool, Sauna Tennis & Trails

Welcome to your perfect all-inclusive Catskills getaway. Secluded hilltop cabin in the woods. Cozy home features heated pool, sauna, large 2000sf deck overlooking forest, full size tennis court, 15.5 acres for hiking, fishing, and exploring. Located only 2 hours from New York City & 20 mins from Woodstock. Two-bdrm house with one full bathroom and loft sleeping space. House is located on a quiet road. Turn into the private driveway and get ready to relax and mingle with Mother Nature

Guest favorite

An inviting in-ground saline pool is surrounded by lush greenery and trees. Sun loungers are placed nearby on a spacious patio, providing a serene outdoor space for relaxation. The pool area is framed by a well-maintained lawn and natural landscaping.

Home in Cottekill

4.95 out of 5 average rating, 280 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.

Top guest favorite

An above-ground saltwater pool is surrounded by a wooden sun deck, featuring two lounge chairs positioned for relaxation. Lush greenery is visible in the background, adding to the serene outdoor setting.

Loft in Prattsville

5 out of 5 average rating, 107 reviews

The Loft at Bearpen Mtn; near Hunter & Windham

Relax in this stylish Mountain View escape at the base of Bearpen Mountain. Hiking trails and snow sports from the front door! Situated near Windham and Hunter; 20 minutes, Belleayre and Plattekill ski mountains, 30 minutes. Walk to winter sports and sledding center. Adjacent to world class trails for hiking, snowmobiling, hunting and skinning. *seasonal rental or multiple stay discounts. $2k per month includes utilities 12/12/25 to 3/15/26 for ski season *no EV charge available

Guest favorite

A serene swimming pond is surrounded by lush greenery and mountain views. Two bright inflatable tubes float on the water, while a dog stands nearby at the water’s edge. The peaceful setting highlights the natural beauty of the landscape.

Cottage in Denver

4.94 out of 5 average rating, 148 reviews

Country Cottage w/ HOT TUB & Views

Welcome to the most peaceful and tranquil place in the world. Our beautiful home is situated on 3 acres of private land with a private pond and incredible views of the mountains. Escape your life and stressors, and come stay in the fresh air where all you will hear are birds chirping - no sirens, cars or people. The cottage is fully stocked to be enjoyed for all 4 seasons! Relax in the hot tub, or go for a swim in the pond. Our property is the perfect vacation getaway.

Guest favorite

Cabin in Lanesville

4.93 out of 5 average rating, 343 reviews

Only Ski In Out on Mtn | Hike, Golf, Fish, Relax

Mountainside 1 bedroom cabin that fits 4! Ski on/off Hunter Mountain right from your doorstep. Enjoy hiking within a 5-minute drive or walk right onto the mountain from your porch. Unbeatable location on Hunter Mountain, short drive to the picturesque, colorful village of Tannersville, majestic Kaaterskill Falls, and renowned fishing! Fully stocked kitchen/bathroom, full entertainment system with streaming, high-speed WiFi, and dedicated work space.