Vacation rentals with a pool in Shawangunk

4.88 out of 5 average rating, 241 reviews

An open living space is visible, featuring wooden beams that create a warm atmosphere. The dining area is filled with natural light, showcasing a wooden table surrounded by chairs, with modern light fixtures above. A staircase leads to the upper floor, enhancing the spacious design.

Home in New Paltz

Scenic River View Escape | New Paltz

Unwind in nature at this scenic New Paltz escape, located on a serene riverbank with spectacular views. Large porch and private backyard are perfect for relaxation and stargazing. Recently renovated, the house blends modern amenities with a tranquil atmosphere. Thoughtfully designed, it features a cozy fireplace, large smart TV, and fully equipped kitchen. Explore nearby hiking trails, waterfalls, and Minnewaska State Park, or relax in the hot tub. Ideal for couples, families, and remote workers

FamilyLocationWalkability

4.88 out of 5 average rating, 222 reviews

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

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

ValueFamilyIndoor spaces

4.99 out of 5 average rating, 279 reviews

An aerial view captures the red dairy barn, featuring a colorful roof with decorative elements. Surrounding greenery and open fields create a serene backdrop, while a winding path leads to the barn entrance, inviting exploration of the surrounding landscape.

Home in Woodstock

The Woodstock Barn House - Sauna, Gym, Jacuzzi

19th Cent Hand-Hewn Dairy Barn. LOVE BIG GROUPS - if your #s exceed 10 we can accommodate. Pet Friendly Inquire for summer dates! IG: @woodstockbarnhouse 2 guest 1 night stays inquire for clean discount Travel & Leisure "Gorgeous Old Catskill Barn" House Beautiful "Best Upstate New York Weekend Destinations " Pool about May to midOct Hot Tub - all year Gym Sauna Fire Pit Projector Tv Pizza Ovens Cabana Kitchen 2 miles from center of town. *No checkin avail Tgiving, Xmas Day, Easter Sunday

LocationValueAir conditioning

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

Entire Home, Private Indoor Pool

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.

LocationValueHeating

4.81 out of 5 average rating, 136 reviews

4.98 out of 5 average rating, 123 reviews

Home in High Falls

Comfortable & Spacious Country Home - All Seasons

We welcome you to stay at our inviting home in the hamlet of High Falls. The two-story early 1900's era farmhouse is set on 12 private acres off a quiet country road in a lovely residential area. Grounds feature access to woods, pond and canoe-ready Roundout Creek. A large sunlit family room, a variety of games, vast outdoor space with furnished patio, in-ground pool/deck/BBQ/swings/firepit/hammock offer the perfect place to relax and restore your connection to nature, friends and family.

FamilyLocationIndoor spaces

4.98 out of 5 average rating, 549 reviews

Home in New Paltz

midcentury mod hot tub*walk out trail R2R/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. IN GROUND SWIMMING POOL & HOT TUB short wooded trail just behind house to access Wallkill Valley Rail Trail, from here walk to an organic farm? A scenic mile to R2R trail to Mohonk, Water St. mkt & the Village of NP WHOLE PLACE IS YOURS HOUSE & PROPERTY POOL May 1 - Sept 21 HOT TUB YEAR ROUND

LocationFamilyParking

5.0 out of 5 average rating, 107 reviews

Home in New Windsor

Historic Cornwall Farmhouse w/ Sauna & Hot Tub

Welcome to The Storm King Farmhouse! Experience the best of upstate living in this beautifully renovated 1800s farmhouse located 50 mi from NYC. The property features a heated pool, Finnish sauna, premium hot tub, pickleball & basketball court, fire pit, pond, and more! Located close to exciting Hudson Valley activities - Storm King Art Center (1 min), West Point (15 min), Legoland (25 min), hiking trails, breweries, etc. This is the perfect place to relax with family & friends! Pet friendly!

LocationFamilyAir conditioning

4.89 out of 5 average rating, 213 reviews

A sheltered outdoor area showcases a large hot tub beneath a wooden gazebo, surrounded by lush greenery. Comfortable seating options, including a hanging chair and two armchairs, offer a space to relax and enjoy the serene landscape.

Cabin in Kerhonkson

Hot Tub - Sauna - Arcade- Fireplace - Pool Open

Welcome to our Catskills oasis on the Rondout Creek and Rail Trail, minutes from Minnewaska and the Gunks! Unwind in the year-round covered hot tub / sauna, lounge by the pool, gather around the fire pit, or play mini golf under the stars. Inside, relax by the fireplace or hit the speakeasy-style game room with pool, pingpong, Pac-Man, Pop-a-shot, darts, a bar, and TV. We offer private chefs, local meats, and top picks for hikes, bites, and watering holes. Yes, we love pets! 🐾

FamilyValueLayout

4.91 out of 5 average rating, 127 reviews

An aerial view showcases a charming farmhouse surrounded by lush greenery and the Catskill Mountains. A rectangular in-ground pool is visible in the backyard, bordered by a grassy area. A quiet country road runs alongside the property, contributing to the tranquil setting.

Home in Grahamsville

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, and picture-perfect fall foliage. Get outside to explore our local trails, parks & lakes. Enjoy a round of golf, or visit the 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.

LocationValueWifi

4.97 out of 5 average rating, 188 reviews

A serene pool area features a deep blue unheated swimming pool with steps leading in. A gazebo, softly illuminated by string lights, is nestled among lush greenery in the background. The natural landscape creates a tranquil retreat.

Apartment in Chester

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 15 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.

ValueLocationComfort

4.94 out of 5 average rating, 413 reviews

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

A Very Cozy House With a Very Big Yard

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.

LocationValueBackyard

4.92 out of 5 average rating, 181 reviews

Home in Beacon

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

Welcome to Hudson Valley Hideaway — a Modern stylish family friendly home in Beacon, NY, just 1.5 miles from downtown and the train. Bright, stylish home with 4 bedrooms, w/ 1 King bedroom, 2 queens and a Twin XL, stocked kitchen, and cozy living spaces. Enjoy a private fenced backyard retreat with pool, hot tub, fire pit, and grill. Perfect for relaxing or exploring the Hudson Valley, with easy access to Route 84 and local attractions.

FamilyLocationHiking

Popular amenities for Shawangunk rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.95 out of 5 average rating, 178 reviews

A spacious living area is centered around a stone fireplace, adorned with wood beams. Natural light filters through large glass doors, offering views of the greenery outside. Comfortable couches are positioned invitingly, creating a relaxing atmosphere for guests.

Home in Cold Spring

Cozy, Modern Retreat in the Woods of Cold Spring

LocationValueView

4.96 out of 5 average rating, 185 reviews

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

Woodstock Historic Artist Estate- The Museum House

LocationFamilyAccess

4.99 out of 5 average rating, 146 reviews

A spacious golf simulator room features a large projection screen displaying a scenic golf course. A putting green is positioned in front, and golf clubs are displayed in the corner. Soft lighting enhances the ambiance, providing a comfortable setting for practice or entertainment.

Home in Lackawaxen

Golf Sim! Hot Tub/Game Room/Cinema 2 Kings

FamilyLocationSkiing

5.0 out of 5 average rating, 122 reviews

An aerial view of BoHo Farm House showcases a modern black exterior with expansive glass panels. The garden features a swimming pool surrounded by lounging chairs and a fire pit, set against a backdrop of lush green grass and trees.

Home in Accord

Design Scandi Retreat, Heated Pool, Dogs Welcome

LocationValueGrill

4.83 out of 5 average rating, 109 reviews

An outdoor pool area features a stone patio surrounded by vibrant flowers and greenery. Lounge chairs are arranged neatly beside the pool, and a wooden cabana is visible with a stone fireplace, creating a relaxing atmosphere for guests.

Home in Philipstown

Gorgeous Garrison Gem Sauna, Spa 5 min Cold Spring

FamilyValueSleep quality

4.93 out of 5 average rating, 126 reviews

A serene outdoor space features a saltwater pool surrounded by lush greenery and fencing. Lounge chairs with brightly colored towels are positioned on the stone patio, inviting relaxation alongside the tranquil water.

Home in Saugerties

Chef’s Kitchen * Screened Porch * Near Woodstock

LocationFamilyDecor

4.92 out of 5 average rating, 118 reviews

The exterior of the home is captured against a clear blue sky, featuring a spacious pool surrounded by stone paving. A large deck with multiple glass doors offers views of the backyard. Lush greenery and trees form a serene setting around the property.

Home in Greenwood Lake

Lake Views | Pool + Hot Tub | 1hr NYC | Ski Access

FamilyValueCheck-in

4.96 out of 5 average rating, 311 reviews

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

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

FamilyLocationLaundry

Condo rentals with a pool

4.96 out of 5 average rating, 167 reviews

Mountain Creek Appalachian Condo Waterpark

FamilyLocationWifi

A spacious living area features a cozy sofa adorned with a throw blanket, set against a stone fireplace. A flat-screen TV is mounted above the fireplace. Nearby, a small dining table with two chairs sits near large windows that offer views of the outdoors.

4.94 out of 5 average rating, 955 reviews

Appalachian Lodge Top Floor w/views

LocationFamilyHospitality

A living area is visible featuring a comfortable sofa, a wooden coffee table, and a television on a media console. A dining area with a wooden table and chairs is positioned near a window, allowing natural light to brighten the space. A decorative fireplace serves as a focal point.

4.89 out of 5 average rating, 231 reviews

Newly renovated Sunset view 1 bedroom

FamilyLocationHiking

4.95 out of 5 average rating, 264 reviews

Best Mtn Views! Mtn Creek Hot Tub Heat Pool #324

LocationValueOutdoor spaces

4.88 out of 5 average rating, 117 reviews

A cozy bedroom features rustic wooden walls with decorative hearts. A spacious bed is dressed in light linens, accompanied by a bedside lamp and a small dresser. A guitar leans against the wall, adding a touch of character to the room.

Condo in Hunter

Cozy Gem with Mountain Views

FamilyValueHiking

A spacious bedroom features a light-coloured bed with neatly arranged pillows. Warm wood accents complement the textured wall behind the bed, while green-framed windows provide natural light and a view of the outdoors. Ambient lighting is created by stylish wall-mounted lanterns.

4.97 out of 5 average rating, 123 reviews

✰ 228 Mountain Creek Luxury Mountain View Sleeps 4

FamilyValueQuiet

4.94 out of 5 average rating, 159 reviews

A spacious living area features large windows offering mountain views. A beige couch with textured cushions sits on a plush carpet. A wooden coffee table is positioned in front of the couch, complemented by a decorative wall hanging. A guitar rests on the floor beside a low bench.

Condo in East Jewett

StunningViews•Bright2BR•Octoberfest•Foliage

LocationFamilyComfort

4.9 out of 5 average rating, 334 reviews

Modern, Upscale Condo at Mountain Creek 1 hr NYC

ValueLocationDecor

Other vacation rentals with a pool

4.99 out of 5 average rating, 198 reviews

Chalet in Olivebridge

Spruced Moose Lodge & Treehouse w/ New Hot Tub!

ValueLocationGrill

4.97 out of 5 average rating, 108 reviews

A spacious two-story house features a covered porch with white railings, providing a welcoming outdoor area. Lush green grass surrounds the property, and the backdrop includes rolling hills and a clear sky with clouds, emphasizing the serene location near the water.

Villa in Greenwood Lake

Hillside villa with 9-mile lake views

LocationFamilyKitchen

4.94 out of 5 average rating, 106 reviews

Cabin in Montgomery

Historic Cabin with Pool and Fire Pit

FamilyLocationBathroom

Cabin in Livingston Manor

An inviting hot tub is positioned on a wooden deck, overlooking a spacious backyard and the tastefully designed home. Soft lighting enhances the outdoor setting as sunset hues paint the sky, creating a serene atmosphere perfect for relaxation.

Experience The Zen House

ValueLocationDecor

4.97 out of 5 average rating, 364 reviews

4.97 out of 5 average rating, 60 reviews

A spacious living area features large windows allowing natural light to fill the room. Two patterned armchairs are positioned beside a sleek coffee table, while a modern sectional sofa offers ample seating. A neutral rug anchors the space, enhancing the cozy, welcoming atmosphere.

Home in New Paltz

Beautiful house under the Gunks

LocationFamilyAccess

5.0 out of 5 average rating, 28 reviews

A vintage stone house is set against a backdrop of trees, showcasing a rustic exterior with large windows and a welcoming entryway. Surrounding boulders and a wooden deck enhance the natural environment, while a covered area is visible to the right.

Home in Pine Bush

Mandell's Escape

LocationFamilySleep quality

4.92 out of 5 average rating, 53 reviews

A serene outdoor space features a private pool surrounded by a well-maintained garden. A koi pond with lily pads adds tranquility, while lounge chairs provide comfortable seating. Lush greenery and colorful shrubs create a peaceful atmosphere, perfect for relaxation and enjoying nature.

Home in Montgomery

Serene Hudson Valley Escape Hottub/Pool/King Suite

ValueLocationAccuracy