
Holiday rentals with a pool in Town of Shawangunk
Find and book unique homes with a pool on Airbnb
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.

midcentury mod * HOT TUB * walk out trail 2 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. fireplace, 5 person hot tub 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 THE WHOLE PLACE IS YOURS- HOUSE, PROPERTY, POOL (open 5/1-9/30) and HOT TUB (open 9/30-5/1)

Modern Upstate Cabin, near Rhinebeck NY
[ 🏊🏽♂️ Heated pool is open May - October 26, 2025. During the colder months we recommend soaking in our giant freestanding tub, which easily fits two humans.] Welcome to Maitopia - our modern, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub for two, a floating fireplace for cozy winter moments and a heated pool. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without 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

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.

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.

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!

Scenic River View Escape | New Paltz
Unwind in nature. House is located on the river bank with river views and surrounded by tall trees with a huge porch and private backyard. The house was recently renovated with all the modern amenities. The place breathes with tranquility and peace and was stylishly decorated with a lot of care and consideration to guests' experience by an experienced host. Just come as you are and enjoy as we have all you need here including top notch complimentary tea, coffee, yoga mats and much more

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.

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.

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.

A Lovely Cottage in the Woods
Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.

Spacious Catskills Farmhouse on over 5 acres!
Come enjoy autumn in the Catskill Mountains! Fall is the best time to visit the Catskills! Crisp nights, fresh apple cider, U-pick farms, bonfires, & picture-perfect fall foliage. Get outside and explore our trails, parks, and lakes or visit the local casino or indoor waterpark. 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.
Popular amenities for Town of Shawangunk rentals with a pool
House rentals with a pool

4Br Mountain Brook House on 130 acres w/ trails

Harrison Field Fall Weekend GetAway ApplePicking

Upstate Modern Scandinavian Barn in the Catskills

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town

Pool Hot tub Sauna Canoe Country Lakehouse

Beautiful house under the Gunks
Beautiful Salt Water Pool & Fully Fenced 10 Acres

Hilltop modern with stunning mountain views
Apartment rentals with a pool

Windham Condo

Hideaway Windham/Hunter Fireplace, Snow & Skiing

206 · Renovated Chic Premium 1 bdrm

Valley Overlook @ Mtn Creek Resort Park & Play

Comfy Studio at Mountain Creek Resort

Appalachian Lodge Top Floor w/views

✰ 255 Mountain Creek Luxury 1 bd Deluxe sleeps 5

Mtn Creek Ski Resort Pool Hot Tubs Sauna Gym #324
Other holiday rentals with a pool

Contemporary 4-BR Catskills Retreat w/ plunge pool

Newly Built Private Home & Pool

Spirit Cabin: Lakefront w/Pool-Sauna-Cold Plunge

Luxe Family Retreat w/ FP, HT & Cabana

BoHo Scandi Farm Retreat, Fireplace, Dogs Welcome

Modern Designer Cabin in Woods w/ 5-star amenities

Mandell's Escape

The Gunks Modern Secluded Home w/ Pool
Quick stats about holiday rentals with a pool in Town of Shawangunk
Total rentals
20 properties
Nightly prices starting at
£52 before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Destinations to explore
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- Rentals with a firepit Town of Shawangunk
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- House rentals Town of Shawangunk
- Rentals with a hot tub Town of Shawangunk
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- Rentals with outdoor seating Town of Shawangunk
- Rentals with a patio Town of Shawangunk
- Rentals with a fireplace Town of Shawangunk
- Family-friendly rentals Town of Shawangunk
- Rentals with pools Ulster County
- Rentals with pools New York
- Rentals with pools United States
- Hunter Mountain
- Mountain Creek Resort
- Bethel Woods Center for the Arts
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- The Kartrite Resort & Indoor Waterpark
- Resorts World Catskills
- Bash Bish Falls State Park
- Kent Falls State Park
- Brotherhood, America's Oldest Winery
- Hudson Highlands State Park
- Walkway Over the Hudson State Historic Park
- Ringwood State Park
- Windham Mountain
- Rockland Lake State Park
- Taconic State Park
- Villa Roma Ski Resort
- Wawayanda State Park
- Sterling Forest State Park
- Great Falls Park
- Mount Peter Ski Area
- Opus 40
- Mohawk Mountain Ski Area