Holiday rentals with a pool in Town of Shawangunk

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Top-rated rentals with a pool in Town of Shawangunk

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

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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
4.83 out of 5 average rating, 110 reviews

Entire Home (private pool), Event Friendly

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.

Superhost
A collage featuring four aspects of the home. The top left displays a cozy living area with a fireplace and comfortable seating. The top right shows a hot tub surrounded by a wooden fence. The bottom left highlights a retro arcade setup with colorful lighting. The bottom right features a dining table set for a meal.
Villa in Kerhonkson
4.88 out of 5 average rating, 110 reviews

Luxe Mountain Getaway|Fire Pit|Arcade|Hot Tub|Pool

Enjoy a luxury nature escape at Boho Chic Villa, under 2 hours’ drive from New York City. This cozy home offers three bright bedrooms, an elegant full kitchen, and unmatched outdoor space. Take a splash in the pool, soak in the hot tub, or make s’mores around the fire pit. Your stay is sure to be an extraordinary experience for the whole family. 6 Min Drive to Minnewaska State Park 8 Min Drive to Kelder’s Farm 10 Min Drive to Stony Kill Falls Experience Kerhonkson With Us & Learn More Below!

Top guest favourite
Flat in Wappingers Falls
5 out of 5 average rating, 232 reviews

Cozy Charming Apartment in Private House ⭐️⭐️⭐️⭐️⭐️

PLEASE READ ALL HOUSE RULES PRIOR TO INQUIRIES AND BOOKINGS! 1 night/longer stays can be accommodated upon request and calendar availability. “Home Is Where The Heart Is”. If you love tranquility and coziness combined with sophistication and traditional rural charm, this is the place for your stay (only 4 miles from Beacon). The ground floor apartment with a private entrance (located around the back in a private house) includes a living room, full kitchen, full bathroom and Queen bedroom

Top guest favourite
A cozy living space is highlighted by a light wooden floor and a white shiplap ceiling. A comfortable brown leather couch and an orange accent chair provide seating. A wooden coffee table sits in front of the sofa. Wall art and a floor lamp add warmth to the room.
Cottage in Kingston
4.93 out of 5 average rating, 395 reviews

Kapitan’s Cottage Private Upstate Catskill Retreat

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.

Guest favourite
An aerial view showcases a modern home surrounded by lush greenery. A curved path leads to the back, where a heated pool is visible, accompanied by outdoor seating and a pergola among the trees. The serene landscape offers a sense of seclusion.
Home in Pine Bush
4.98 out of 5 average rating, 106 reviews

Hudson Valley Oasis - Sauna, Hot Tub, Heated Pool!

A modern oasis in the Hudson Valley near hiking, skiing, apple-picking, antiquing, and other fun seasonal activities only 1.5 hours from NYC. Enjoy swimming in a heated pool? Great! We have a beautiful pool (Opens 4/1) and pool house complete with an outdoor bar and hot tub. Lovely outdoor garden with a fire pit nestled in the middle. A patio with a gas grill and pizza oven is ready for all chefs. We feature a three-person sauna inside! Just secluded enough to be perfect for larger gatherings!

Guest favourite
A cozy sleeping area features a queen-size bed dressed in a red and black plaid comforter. Two lamps are positioned on either side, providing soft lighting. A small nightstand holds decorative items, while a trunk for storage is located at the foot of the bed.
Loft in Mountainville
4.84 out of 5 average rating, 605 reviews

Country Getaway - Close to Hiking & Storm King

Enjoy the countryside minutes away from downtown restaurants, bars and Main Street, in our private, cozy loft studio! Located on 1.5 acres, this clean and comfortable apartment includes a kitchenette with bar-style table, living room and two flat screen Roku TV’s with Netflix, Hulu as well as an electric fireplace, outdoor patio and fire pit. Guests have two parking spaces, a private first-floor entrance, private full bathroom, outdoor dining area, BBQ and fire pit! Pool available seasonably.

Superhost
The collage showcases different areas of the home and yard. An outdoor seating area with a pergola and hot tub invites relaxation, while a spacious pool lies in the background. The living area features a cozy setup with a Peloton bicycle, and the kitchen area includes a bar, enhancing social gatherings.
Cottage in Kerhonkson
4.81 out of 5 average rating, 199 reviews

Gunks Cottage|Fire Pit|Pool|Near Minnewaska Park

This charming 2-bedroom cottage is nestled on an acre of private, untouched wilderness, making it a great place for nature lovers, hikers, and couples looking for the perfect getaway. When you’re not exploring Minnewaska State Park, enjoy the pool, stargazing from next to the fire pit, and soaking tired muscles in the hot tub. 6 Min Drive to Minnewaska State Park Preserve 10 Min Drive to Stony Kill Falls 15 Min Drive to Wightman Fruit Farm Experience Kerhonkson With Us & Learn More Below!

Guest favourite
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, 166 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 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
4.96 out of 5 average rating, 289 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 favourite
A small red cabin is framed by lush greenery, with a welcoming porch featuring two wooden rocking chairs. Natural stone path leads to the entrance, surrounded by a forest of tall trees and soft moss-covered ground.
Cabin in New Paltz
4.95 out of 5 average rating, 157 reviews

Le Petit Abris at Gunks EcoLodge

Now open in Winter, but subject to refunded cancellation if Snow makes the driveway unpassable for those without 4 or all wheel drive. This rental is a small cabin in the woods of New Paltz, NY. The cabin sleeps 4 with 2 twin beds in the loft and has a pullout couch with a quality queen size mattress. The kitchen is equipped but does not have an oven. Streaming TV and Internet. Check out our other listings at the EcoLodge, with Private Rooms/Baths, on the "About Me" page.

Top guest favourite
A spacious main area is highlighted by a large bed covered with a floral quilt. A comfortable sofa is positioned nearby, while a wooden café counter with four chairs overlooks natural light coming through the three windows. A coffee bar and kitchen appliances are integrated into the space.
Flat in New Paltz
4.93 out of 5 average rating, 370 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!

Guest favourite
A spacious main room is featured with high ceilings and a skylight. The kitchenette is visible alongside a dining table and chairs. A wooden coffee table sits in the living space, adorned with decorative items. Natural light flows through large windows framed by greenery.
Flat in Chester
4.98 out of 5 average rating, 142 reviews

Private Country Getaway

This family-friendly apartment is an hour from NYC, with a private driveway and entrance. The location is ideal for a getaway in any season. In the Warwick Valley, the property is 10 min from Legoland, and 13 min from the NY Renaissance Festival, surrounded by vineyards, orchards, farms, breweries, state parks, skiing, and the Appalachian Trail. 5 minutes from historic Sugar Loaf and the Sugar Loaf Performing Arts Center. 15 min from Woodbury Commons Premium Outlets.

Popular amenities for Town of Shawangunk rentals with a pool

Quick stats about holiday rentals with a pool in Town of Shawangunk

  • Total holiday rentals

    Explore 20 holiday rentals in Town of Shawangunk

  • Nightly prices starting at

    Town of Shawangunk holiday rentals start at £53 per night before taxes and fees

  • Verified guest reviews

    Over 1,240 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Town of Shawangunk holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Town of Shawangunk rentals

  • 4.9 Average rating

    Town of Shawangunk stays are highly rated by guests – averaging 4.9 out of 5!

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