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Vacation rentals with a pool in Shawangunk

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Shawangunk

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

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Cottage in Pine Bush

4.89 out of 5 average rating, 228 reviews

Seclusion and romance and free drinks!

Amazing 5 Star guest house. Free electric car charging both telsa and all others! Outdoor living room with a wood fireplace. Close to many Hudson Valley attractions: hiking, wineries, breweries, restaurants, Sam's Point, etc. Very romantic, high end getaway. Amenities: charcoal BBQ, mini fridge, propane grill, full bath, microwave, wood fireplace, fire pit, single induction hot plate, wifi, smart TV, Firewood and fire bricks available. The pool will be closing the week of October 16th 2023.

Jan 12 – 19

R5,802 ZAR per night

Home in Stormville

4.94 out of 5 average rating, 156 reviews

Private Hudson Valley Country Retreat

Beautiful 1930s house set on 18 private acres of land overlooking a private lake. Immaculately landscaped surrounding area with koi and gold fish pond with a waterfall, gazebo, hammock and most importantly untouched nature. Very private! Enjoy your morning coffee or tea in the outdoor covered patio overlooking the property, wine and dine under the pergola, enjoy the fire pit or wood burning fireplace on a chilly evening. Serenity and relaxation at its best! Pond dock coming up in Spring of 2021

Oct 20 – 27

R14,881 ZAR per night

Cabin in Kerhonkson

4.82 out of 5 average rating, 213 reviews

Heated Pool/Sauna/Tennis: Hilltop Secluded Retreat

Welcome to your perfect all-inclusive Catskills getaway. Secluded hilltop cabin in the woods. Cozy home features salt-water 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

Jun 21 – 28

R7,949 ZAR per night

Home in Cold Spring

4.95 out of 5 average rating, 152 reviews

Cozy, Modern Retreat in the Woods of Cold Spring

Newly renovated with modern style and amenities yet retaining all of its rustic warmth and charm, our home is perfect for your next get away. Outdoors, enjoy the salt water pool, patio, grill and fire pit in our secluded setting. Indoors we offer a sauna, steam shower, central heat and air, a woodburning fire place, crib and baby monitor, ping pong table, washer and dryer, and a fully loaded kitchen. Located 7 minutes drive from charming Cold Spring and just across the river from West Point.

Oct 25 – Nov 1

R10,243 ZAR per night

Apartment in Wappingers Falls

5.0 out of 5 average rating, 174 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.

Jun 21 – 28

R3,813 ZAR per night

Cottage in Kerhonkson

4.84 out of 5 average rating, 141 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!

Sep 19 – 26

R8,000 ZAR per night

Home in New Paltz

4.98 out of 5 average rating, 436 reviews

midcentury modern in ground pool walk 2 trail/town

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. short wooded trail just behind house to access Wallkill Valley Rail Trail, from here walk a scenic mile to R2R trail Water St. mkt & the ❤️ of New Paltz Village. Several outdoor seating areas. The whole place is yours FULL PRIVATE ACCESS TO HOUSE/PROPERTY POOL OPEN MAY 1 - end of SEPTEMBER

Sep 6 – 13

R17,289 ZAR per night

Home in Woodstock

4.98 out of 5 average rating, 100 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..

Dec 2 – 9

R15,099 ZAR per night

Cabin in New Paltz

4.97 out of 5 average rating, 137 reviews

New Paltz dog friendly retreat w/salt water POOL

New Paltz dog friendly retreat is a wonderful place to explore the Hudson Valley. 7min drive to downtown New Paltz. 10min to Minnewaska state park & Mohonk preserve. Our very large fenced yard & heated 27ft salt water pool is for your private use during your stay. A signed pool waiver will be required. Heating pool fee is $20 daily. Dog fee $100 per dog. Carolyn whom lives on site in a completely separate studio is there to trouble shoot any issues & keep the pool sparkling clean.

Oct 17 – 24

R8,081 ZAR per night

Home in Kerhonkson

4.94 out of 5 average rating, 325 reviews

Country House: Rustic Charm With Modern Feel

Look from the luxurious spa tub at the countryside oasis atop a rolling knoll on the edge of fir-scented forest land. Come home from a hike, farm, or award winning restaurant, & snuggle up by the fire under grand cathedral ceilings. In summer, swim in the salt water pool & enjoy the fire pit surrounded by lush landscaping & quiet. Stunning views as the seasons change, the windows showcasing rolling snowy hills or the vibrant colors of autumn leaves climbing the mountains.

Aug 26 – Sep 2

R16,491 ZAR per night

Chalet in Olivebridge

4.98 out of 5 average rating, 124 reviews

Spruced Moose Lodge & Treehouse w. Hot Tub & Pool!

Secluded log home on 5 acres, beautifully situated at the top of a no outlet road on a mountainside in the Catskills. The home has 4 bedrooms + 3.5 baths, with the 4th bedroom being a finished basement that has built-in full size bunk beds. There is also a sunroom, screened porch, pool, hot tub, and a treehouse that resembles a floating pirate ship 30 feet up in the trees. Town of Olive Registration No: STR-23-2 SEC-BLK-LOT: 52.4-1-5.500

Sep 30 – Oct 7

R12,573 ZAR per night

Guest suite in New Paltz

4.94 out of 5 average rating, 299 reviews

Airy & Private Escape on Mountain Rest Road *Pool*

Relax and unwind in our bright and private 2BR apartment located at the edge of Unison Arts Center’s sculpture garden (paths through woods and fields). A mile from New Paltz on the way to Mohonk Preserve, this simple but comfortable space features work by local artists and regional photographs. One of the bedrooms has an additional half-bathroom with a hand-made mosaic. Guests have their own entrance.

Aug 13 – 20

R3,626 ZAR per night

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Popular amenities for Shawangunk rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Cottekill

4.95 out of 5 average rating, 242 reviews

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

Sep 30 – Oct 7

R6,721 ZAR per night

Home in Middletown

4.94 out of 5 average rating, 100 reviews

Springtime farm escape with hot tub and amenities

Dec 21 – 28

R4,927 ZAR per night

Home in New Paltz

4.93 out of 5 average rating, 121 reviews

Harrison Field Enquire For Heated Pool Bike 2 Town

Oct 9 – 16

R14,997 ZAR per night

Home in Stamford

4.97 out of 5 average rating, 220 reviews

Midcentury Modern ZenHouse Sculptor Studio

Dec 24 – 31

R7,148 ZAR per night

Home in Narrowsburg

4.97 out of 5 average rating, 141 reviews

Modern Ranch With Pool & Hot-Tub

Sep 9 – 16

R9,041 ZAR per night

Home in Downsville

4.97 out of 5 average rating, 110 reviews

Trout fishing on the Delaware

Jan 5 – 12

R2,813 ZAR per night

Home in West Milford

4.99 out of 5 average rating, 113 reviews

On The Rocks In The Hot Tub

Nov 14 – 21

R7,099 ZAR per night

Home in Rhinebeck

4.96 out of 5 average rating, 164 reviews

On The Hill in Rhinebeck

Dec 22 – 29

R10,547 ZAR per night

Condo rentals with a pool

Condo in Vernon Township

4.97 out of 5 average rating, 144 reviews

Comfy Studio at Mountain Creek Resort

Jan 30 – Feb 6

R1,923 ZAR per night

Condo in Vernon Township

4.95 out of 5 average rating, 238 reviews

NYC Escape 1 hr away

Aug 13 – 18

R3,405 ZAR per night

Condo in Vernon Township

4.95 out of 5 average rating, 729 reviews

Appalachian Lodge Top Floor w/views

Oct 20 – 27

R3,231 ZAR per night

Condo in Vernon

4.8 out of 5 average rating, 118 reviews

Budget friendly Sunsets Pool Hot Tubs Sauna 259

Jan 27 – Feb 3

R2,406 ZAR per night

Condo in Vernon Township

4.97 out of 5 average rating, 216 reviews

Rustic Chic at Mountain Creek! Pool|Hot Tub|Sauna

Jul 2 – 9

R4,374 ZAR per night

Condo in Vernon Township

4.9 out of 5 average rating, 301 reviews

Appalachian TOP 4TH FLOOR Studio+ w/amazing views!

Dec 12 – 19

R2,836 ZAR per night

Condo in Vernon Township

4.76 out of 5 average rating, 137 reviews

1 Bedroom Condo @ Appalachian Resort Hotel

Sep 22 – 29

R2,699 ZAR per night

Condo in Vernon Township

4.94 out of 5 average rating, 102 reviews

Resort Getaway-Mtn Creek Ski/Pool/Hot Tub/Sauna

Jun 14 – 21

R3,803 ZAR per night

Home rentals with a private pool

Home in Lagrangeville

4.84 out of 5 average rating, 120 reviews

Classic Hudson Valley Farmhouse Nestled in 9 Rolling Acres

Sep 27 – Oct 4

R11,411 ZAR per night

Farm stay in Fleischmanns

4.91 out of 5 average rating, 11 reviews

Escape to a Dreamy 1857 Farmhouse in Fleischmanns

Feb 19 – 26

R7,602 ZAR per night

Home in Rhinebeck

5.0 out of 5 average rating, 65 reviews

Rhinebeck Country Living with a Modern Twist

Jun 26 – Jul 3

R13,211 ZAR per night

Home in Woodstock

4.6 out of 5 average rating, 10 reviews

Luxury Retreat in the Catskills

Aug 29 – Sep 5

R21,152 ZAR per night

Home in Lanesville

4.77 out of 5 average rating, 205 reviews

Go Hiking and Skiing from a Family-Friendly Farmhouse

Mar 10 – 17

R7,905 ZAR per night

Quick stats about vacation rentals with a pool in Shawangunk

Total rentals
30 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
1.1K reviews
Nightly prices starting at
R2,227 ZAR before taxes and fees

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