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Home rentals with a pool near Windham Mountain

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool near Windham Mountain

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Top guest favorite

An inviting outdoor space features a sparkling pool surrounded by a spacious deck. Sun loungers are positioned nearby, while majestic mountain views extend in the background. Clear blue skies provide a bright ambiance, enhancing the tranquil setting.

Home in Germantown

4.95 out of 5 average rating, 133 reviews

Hilltop modern with stunning mountain views

Beautiful modern residence with a pool & fireplace in Germantown. Fantastic as a weekend getaway or longer-term rental. In the front, stunning mountain views wrap around the master bedroom, kitchen, living room and deck. Out back, a spacious yard and rolling hills. Grill & eat on the big pool deck, lounge in chaises. Fully equipped kitchen, washer & dryer, and *fast wifi*. Perfect for remote work, and each space has its own desk. Shop, walk, hike, ski: Close to Hudson, Olana & Catskills.

A cozy bedroom features a spacious bed with a patterned quilt. Bright natural light fills the room through large windows, complemented by soft window treatments. A comfortable chair, wooden dresser, and wall-mounted television add to the inviting space's functionality and warmth.

Townhouse in Windham

4.89 out of 5 average rating, 153 reviews

Amazing + pet friendly gem in the heart of Windham

Amazing 2 floor spacious getaway with A/C just minutes away from Windham Mountain ski resort, hiking trails, and great restaurants. Family friendly home with a large inviting living room, 2 spacious bedrooms, 2 full bathrooms and wood burning fireplace. Updated kitchen appliances, super-fast Wi-Fi and 3 smart TV's. Many extras including parking, 2 tennis courts, swimming pool and firepit. BBQ Grill on private back deck with scenic views. Winter season rentals preferred during Dec - March.

Top guest favorite

Condo in Windham

4.9 out of 5 average rating, 210 reviews

Hideaway Windham/Hunter Fireplace Autumn & Foliage

Spacious 1BR condo for a max. of 4 guests , sleeps 2 in separate bedroom , additional 2 on an inflatable airbed . Balcony with mountain view ,2 tennis courts ,outdoor pool . Awesome location . Windham and Hunter within reach .Get close to nature in the nearby hiking trails, Windham Path, Kaaterskill Falls. Kayaking on North-South Lake or ziplining in Hunter,skiing ,snowboarding ,golfing and mountain biking . Leave your worries at home and come to relax.Enjoy many dining options in town.

Cabin in Lanesville

4.93 out of 5 average rating, 338 reviews

Exclusive Pool, Mtn Views! Hike, Golf, Swim, Relax

Mountainside 1 bedroom cabin that fits 4! Enjoy hiking within a 5-minute drive or walk right onto the mountain from your porch. Exclusive access to a seasonal pool with stunning mountain views (Memorial Day–Labor Day). 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.

An outdoor swimming pool is surrounded by a secure fence and shaded by tall trees. Several lounge chairs are positioned around the pool area, and blue umbrellas provide shade. Clear blue water reflects the sky above, inviting relaxation.

Condo in Windham

4.66 out of 5 average rating, 119 reviews

Windham Condo

This condo is right off Route 23, minutes from Windham Mountain. Head to the Catskills to enjoy the great outdoors. The complex has a pool, 2 tennis courts and a fire pit. Enjoy the mountain air while working from home with dedicated Wifi. We have a well-stocked kitchen, wood-burning fireplace, and comfy deck. You are in place to enjoy all the skiing, hiking, mountain biking, and golf Windham has to offer. Only 2.7 miles from Windham Mountain Resort. Guest ID may be required on arrival.

Top guest favorite

Cabin in Shandaken

4.96 out of 5 average rating, 207 reviews

Camp Catskills: Heated Pool I Fire-Pit I Hot Tub

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!

Home in Woodstock

4.97 out of 5 average rating, 156 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 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, 106 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

A clear swimming pool is enclosed by a fence, featuring a ladder for easy access. Lush greenery and the mountains are visible in the background, with lounge chairs positioned nearby. The scene is set under a bright blue sky with wispy clouds.

Condo in East Jewett

4.93 out of 5 average rating, 135 reviews

MountainViewBrightCondo10MinToColgateLake

Sunny and spacious condo with stunning mountains view, a perfect place to disconnect from busy life . Plush and comfortable decor , fire place , plenty of board games - perfect set up for a group or a family to unwind in the mountains, gather for home cooked dinner and drinks. Spacious deck is a sweet spot to enjoy morning coffee and listen to the frog songs. Swimming pool (communal for residents and renters only )seasonal , NOT heated, opens in June 28through September 5th.

A wooden deck is furnished with comfortable seating and a coffee table, providing a serene view of rolling mountains and a tranquil pond. The sky is filled with fluffy clouds, reflecting warm hues as the sun sets, enhancing 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.

Top guest favorite

The exterior view showcases two townhouse units set against a backdrop of rolling hills and clear blue skies. A sprawling lawn, dotted with trees, provides open green space. Features include a stone pathway leading to the units and a fire pit area visible in the distance.

Townhouse in Windham

4.9 out of 5 average rating, 125 reviews

Windham Mountain Village 2 bedroom townhouse

This 2 bedroom, 2 bath Townhouse with loft that sleeps 8 (max 6 adults) is located at the top of Windham Mt Village a very short walking distance from the Windham ski lodge and beginner lifts. Fully equipped kitchen, dining area, living area with fireplace including firewood. TV with cable and free high speed wifi. Outdoor deck with gas grill. Washer and Dryer. 2 parking spots in front. Access to community pool and hot tub when open. Air Conditioning in summer.

The outdoor pool is surrounded by a fenced area with lounge chairs positioned around its perimeter. Lush greenery and trees provide a natural backdrop, with a shaded umbrella nearby. A storage shed is visible in the background, adding to the functional outdoor space.

Townhouse in Windham

4.84 out of 5 average rating, 203 reviews

Redwood Retreat in Windham - minutes to Mtn!

True mountain getaway, just 2.5 hours from NYC!! Spacious 2 bedroom 2 bathroom townhouse minutes to Windham Mountain. Enjoy beautiful wood-burning fireplace, Roku TV and high speed Wi-Fi perfect for remote work. Amenities include outdoor pool (open from Memorial through Labor Day), pickleball, basketball and tennis courts, as well as a fire pit with Adirondack chairs. Very close to town and the amazing escarpment hiking and Elm Ridge mountain bike trails.

Popular amenities for rentals with a pool near Windham Mountain

Free parking on premises

Air conditioning

House rentals with a pool

An above ground pool is situated in a spacious yard surrounded by lush greenery. The pool's clear blue water reflects the sky, while a nearby patio area is equipped with seating and umbrellas. A charming red house serves as a backdrop, completing the serene outdoor scene.

Home in Windham

4.95 out of 5 average rating, 85 reviews

Spacious Villa, 6bdrm, Pool, Movie Room, Hot Tub

Aerial view of the Catskills lake-front house surrounded by greenery, showcasing the serene lake and lush forested area. The property features a large driveway, with the house positioned near the water's edge. Tranquil lake views extend into the distance.

4.93 out of 5 average rating, 153 reviews

Private lakefront home, hot tub & resort amenities

Home in Saugerties

4.86 out of 5 average rating, 137 reviews

Shaggerties - fun cozy catskill mountain getaway

The spacious bedroom features a large bed with a geometric patterned duvet and plush pillows. Flanking the bed are two nightstands with lamps. A cozy area rug complements the hardwood floor. Robes are hung on the wall, and a doorway leads to the en suite bathroom.

Home in Saugerties

4.93 out of 5 average rating, 138 reviews

Bluestone Escape - Where everyone is at home.

The exterior of the house showcases a modern design framed by lush greenery. A spacious deck surrounds the heated saltwater pool, equipped with lounge chairs and an umbrella for shade. The contrasting white walls and dark roof enhance the inviting atmosphere.

Home in Roxbury

4.95 out of 5 average rating, 80 reviews

Canopy Hill House - Modern w/ Pool+Hot Tub+Mt View

A tranquil saltwater pool is set against a natural stone backdrop, surrounded by lush greenery. Poolside, a sunbed and umbrella are positioned, providing a relaxation spot. The patio features a rugged stone surface, enhancing the outdoor experience amidst a serene atmosphere.

Home in Saugerties

4.88 out of 5 average rating, 111 reviews

Highwoods Haven | saltwater pool and hot tub

An inviting in-ground heated swimming pool is surrounded by a spacious stone patio, featuring six lounge chairs and a circular dining table with four chairs. A large umbrella provides shade, and a red barn is visible in the background, framed by greenery.

Home in Saugerties

4.94 out of 5 average rating, 155 reviews

5BR close to Village | Diamond Mills | HITS | Pool

A spacious deck features two comfortable chairs and a round table at its center, offering a clear view of the expansive Catskill Mountain landscape. Lush greenery and rolling hills stretch into the distance under a bright blue sky.

Home in Stamford

4.98 out of 5 average rating, 123 reviews

Hawk View

Condo rentals with a pool

Top guest favorite

An outdoor swimming pool is surrounded by a chain-link fence, featuring clear blue water and several white lounge chairs positioned beside the pool. Lush green grass and trees frame the area, with a view of a red building in the background.

Condo in Hunter

4.88 out of 5 average rating, 93 reviews

Cozy Gem with Mountain Views

Top guest favorite

An outdoor heated pool is surrounded by a spacious patio, with two hot tubs nearby. Lush greenery and vibrant autumn foliage create a scenic backdrop. Multiple lounge chairs are positioned along the poolside, inviting relaxation in a serene setting.

Condo in Windham

5 out of 5 average rating, 25 reviews

Luxury. 5-Star. Ski In/Out, Heated Pool, Hot Tub

A spacious balcony offers a view of a well-maintained pool surrounded by greenery. The landscape features a variety of trees displaying autumn colors and mountains in the distance, with clear blue skies above.

Condo in Windham

4.92 out of 5 average rating, 12 reviews

Luxury 3-bedroom Condo on Windham mountain

A welcoming living area features large glass doors offering views of the outdoors, with natural light enhancing the space. A comfortable seating arrangement includes a dark blue chair and a sectional sofa, while a stylish large area rug adds warmth. Decorative elements include wall art and a blooming floral arrangement.

Condo in East Jewett

4.94 out of 5 average rating, 32 reviews

Hunter & Windham: Hikes, Lakes, Pool, 2BR

A spacious living area is illuminated by large windows showcasing mountain views. A comfortable sofa and two plaid chairs are arranged around a wooden coffee table. Warm light is provided by a standing lamp, and a flat-screen TV sits on a brick fireplace console.

Condo in Lanesville

Hunter Mountain 2BR Penthouse | Vaulted Ceilings

An indoor pool area is showcased, featuring a large swimming pool with clear blue water. Sunlight filters through multiple windows, illuminating the space. Wooden beams and a high ceiling create a spacious atmosphere, complemented by seating options along the poolside.

Condo in Windham

4.92 out of 5 average rating, 61 reviews

4 Bedroom Condo, Close to Golf Courses and Biking

A spacious living area is highlighted by large windows that provide views of the surrounding landscape. A modern fireplace is set against a stone feature wall, while comfortable seating options include a sectional sofa and accent chairs. A flat-screen TV is mounted above a stylish entertainment unit.

Condo in Windham

5 out of 5 average rating, 3 reviews

Windham Mountain Ski In Ski Out - Pool Hot Tub Gym

An aerial view captures the Whisper Creek condo set against a snowy mountain backdrop, with ski slopes winding down the hillside. The landscape features a mix of pine trees and winter terrain, while the luxury building connects to the scenic outdoors.

Condo in Windham

5 out of 5 average rating, 6 reviews

Luxury Ski in Ski out Condo + Amenities

Other vacation rentals with a pool

A comfortable living area features a stone fireplace and large windows, allowing for ample natural light and views of the outdoors. A sectional sofa and a coffee table provide seating, while a ceiling fan circulates air. Decorative accents include vibrant cushions and wall art.

Townhouse in Hunter

4.91 out of 5 average rating, 155 reviews

Summer Mountain Stay at THE Ideal Hunter Home

An indoor pool is featured within a spacious facility, surrounded by light wooden paneling. Large windows allow natural light to illuminate the clear water, and upright black chairs are positioned along the side, providing seating for guests.

Townhouse in Windham

4.97 out of 5 average rating, 70 reviews

Red Lift Cabin - close to town, biking, hiking

Top guest favorite

Home in Catskill

4.98 out of 5 average rating, 63 reviews

Hudson Valley & Catskill Mountain Views • Hot Tub

A bright living area features a modern chaise lounge positioned near a stone fireplace. Natural light filters through the nearby window. A tasteful textile hangs on the wall, and a small table sits beside the lounge, adding functionality to the serene space.

Townhouse in Windham

5 out of 5 average rating, 12 reviews

All-Season Condo-Ski Windham | Pool | Hike | Fish

Top guest favorite

Chalet in Elka Park

4.97 out of 5 average rating, 103 reviews

Thorne Hollow - Mountain Ski Getaway with HotTub

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, 152 reviews

Secluded Woodstock Retreat with Pool and Sauna

An indoor swimming pool is surrounded by stone walls and features a wooden ceiling that adds warmth to the space. Windows allow natural light to illuminate the tranquil water, while safety signage is visible near the pool's edge.

Townhouse in Windham

4.98 out of 5 average rating, 96 reviews

Cozy, peaceful-3Br (5 beds)2.5 Bath townhouse

A heated plunge pool is centered in the image, surrounded by a spacious outdoor area featuring seating arrangements, including lounge chairs and a picnic table. A sunshade is visible, along with scenic mountain views and greenery in the background.

4.94 out of 5 average rating, 171 reviews

Mtn View Lux Dome w/ Heated Plunge Pool

Destinations to explore