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Vacation rentals with a pool in Windham

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Windham

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

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A serene outdoor scene features a reflecting pool surrounded by a grassy area. A wooden barn stands in the background, partially shaded, with a deck area furnished with lounge chairs. Lush greenery is visible in the surrounding landscape under a partly cloudy sky.

Tiny home in Ghent

4.95 out of 5 average rating, 131 reviews

Country Getaway Tiny House in Woods w/Pool/Sauna.

Tiny Small House - 600 Sq ft. of new living space on 30 private acres with walkable trains in Beautiful Columbia County. Secluded privacy surrounded by nature. House has everything you need and sleeps 4 with two twin loft beds. Enjoy the pool and renovated barn pool house. In the Winter stay warm by the wood stove. Enjoy the 6 person sauna year round. Restaurants close by or stay in and enjoy the property. Located 9 miles from Hudson and 3 miles from Chatham and Kinderhook. Near OMI Arts Center.

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

4.94 out of 5 average rating, 126 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.

The outdoor area showcases a seasonal heated pool surrounded by a safety fence. Colorful inflatable pool toys and a waterslide are visible. Sun loungers sit on a wooden deck, with lush greenery framing the space, creating a serene and inviting atmosphere for relaxation.

Home in Saugerties

4.94 out of 5 average rating, 68 reviews

Perfect Family Retreat•Pool•Volleyball•Firepit

This stylish, 3-bed, 2-bath home has a plethora of amenities that will keep the kids occupied for hours any time of the year, including a large kids play area in the lower level of the house and a large back yard w newly built FIREPIT area. Close to ski & a back field to build snowmen & sled in winter. In summer, a seasonal heated pool, waterslide & child safety fence, tree house, beach volleyball crt, swing set. Saugerties 10 mins. Relax with the whole family at this peaceful place to stay.

An outdoor patio area is showcased, featuring a sparkling pool surrounded by a faux stone deck. Comfortable wooden lounge chairs and a coffee table are positioned near the pool, with a hot tub visible in the background. Lush green hills stretch into the distance under a clear blue sky.

Home in Catskill

4.9 out of 5 average rating, 104 reviews

Pool*Hot Tub*Pirate Ship*Fire Pit*Luxury Farmhouse

Welcome to our Stunning 4-Bedroom, 4-Bathroom Modern Farmhouse with Private Pool, Hot Tub, and Amazing Views! - Newly Re-Built (2023) - Tastefully Decorated, Modern Finishings - Amazing Mountainside Panoramic Views, Lots of Sunlight - Over 2,000 Square Feet of Outdoor Patio Space (BBQ, Fire Pit, Games) - 5min to I-87 & Catskill Downtown, 15min to Hudson (Amtrak), 25min to Windham (Ski/Golf), 35min to Hunter Ski Area Perfect for Vacationing, Entertaining, Group Retreats and Family Gatherings!

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

4.88 out of 5 average rating, 144 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.

A clear, blue saltwater swimming pool is surrounded by lush greenery and tall trees. Lounge chairs are positioned by the poolside, with a stone path leading to the water. The tranquil setting provides a sense of privacy and relaxation.

4.93 out of 5 average rating, 243 reviews

Casa Luna Country Retreat with Pool, Hudson, NY

CASA LUNA Perfect peaceful upstate NY country retreat. An all year round escape. 2 hours from NYC driving or Amtrak. 15 mins to downtown Hudson with great restaurants and shopping. 20 mins to water skiing on Copake Lake and 25 mins snow skiing at Catamount, Berkshires. Private & secluded. Columbia County, New York. 4 bedrooms, 2.5 bathrooms, salt water swimming pool, koi pond, claw foot bath tub, steam room. If CASA LUNA is booked check CASA SOL https://www.airbnb.com/rooms/1627143

Top guest favorite

The exterior of a modern cabin is displayed, featuring large glass windows and a sleek black facade. A heated pool is visible with a smooth blue surface. Several lounge chairs are arranged around the pool, enhancing the outdoor relaxation space.

Cabin in Red Hook

4.96 out of 5 average rating, 348 reviews

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open May - October. 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.

Top guest favorite

A serene outdoor space features a private in-ground pool bordered by a travertine patio, accompanied by lounging chairs. A charming purple poolhouse stands nearby, while the multi-story house is illuminated under the evening sky, surrounded by lush greenery and vibrant flowers.

Townhouse in Hudson

4.95 out of 5 average rating, 211 reviews

Palazzo Hudson: Luxury Home with Pool, Spa, Sauna

Welcome to Palazzo Hudson! The only private vacation home in the town of Hudson with a chef's kitchen, seasonal in-ground pool, deluxe sauna, cedar hot tub & a separate poolhouse library lounge. A home for all seasons, you'll experience inspiration and relaxation from the warm, light-filled rooms, curated art, books, music, luxury spa features, and outdoor deck, patios, and gardens. A quick stroll to the restaurants, bars, cafes, and shops of Warren Street and the Upper Depot District.

A large heated swimming pool is surrounded by lush greenery, with several lounge chairs arranged on a concrete deck. A float in blue and white lies on the water's surface, and an umbrella provides shade nearby.

Apartment in Saugerties

4.97 out of 5 average rating, 111 reviews

Lovely Creekside w pool/sauna near Woodstock

This 2-room apt overlooks a flowing stream and includes: bedroom, full kitchen, bath, living room, laundry, deck and use of large heated swimming pool. A beautiful setting very convenient to Woodstock and Saugerties - 3 miles from the NYS Thuway Exit 20, very close to HITS and 30 minutes from skiing at Hunter Mountain. We are carbon neutral, with geothermal and airsource heat pumps, large solar array, and a Level 2 EV charger for our guests. Nosotros hablamos un poco de español

A central living space features a spiral staircase and high cathedral ceilings supported by wooden beams. Light streams through large windows, illuminating a mix of white sofas and chairs positioned on a natural fiber rug. The open layout connects to the kitchen area in the background.

Home in Stanfordville

5 out of 5 average rating, 5 reviews

The Round House w/ Heated Pool

Make some memories at this unique and family-friendly estate. Private & secluded on over 20 acres with heated inground pool this spacious 4 bed, 2 full baths, plus den with sleeping sofa has plenty of space for all. Park-like grounds featuring open fields, picturesque stonewalls overlooking beautiful, heated pool and expansive stone patio where you can entertain or just relax and enjoy nature. Discover effortless living in this fun yet chic dwelling in a remote natural setting.

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

4.95 out of 5 average rating, 355 reviews

Beautiful Salt Water Pool & Fully Fenced 10 Acres

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.

A private saltwater pool is surrounded by lush greenery, featuring a smooth stone deck. The clear blue water invites relaxation, while steps lead into the pool. Trees provide natural shade along the perimeter, creating a serene outdoor setting.

Home in Woodstock

4.86 out of 5 average rating, 132 reviews

Gorgeous Villa Mntn Views, salt H2O pool, hot tub!

Our beautiful Villa has amazing mountain views, a clean, modern design and is the perfect getaway to socialize & relax. It is ideally located for hiking & has a gorgeous, private salt water pool (mid May- mid Oct) and a wonderful hot tub which is open year round! Please check for pool opening/closing. In addition to the main house there is also a spacious studio cottage (with bathroom) & heat that can be used as a WFH private office. It has it's own high speed internet.

Vacation rentals for every style

Get the amount of space that is right for you

Chalets

Adventure-ready homes with après-ski style

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A space thats all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Windham rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

The exterior view showcases a red house surrounded by a large green lawn and mature trees. Autumn colors are displayed in the foliage, with blue skies and clouds above. Several vehicles are parked near the house, which features multiple sections connected by landscaped areas.

Home in Saugerties

5 out of 5 average rating, 12 reviews

The House on the Hill

A heated salt-water pool is surrounded by greenery, with lounge chairs positioned nearby. A bright yellow rubber duck floats on the water, while the pool is bordered by textured pavers. Tall trees provide a natural backdrop, ensuring privacy and tranquil views.

Home in Woodstock

4.86 out of 5 average rating, 211 reviews

Lux Woodstock Pool/ Pvt/Fireplaces /4 mins 2 town

Top guest favorite

A private pool is surrounded by timber decking, complemented by sleek lounge chairs and vibrant umbrellas for shade. The modern home in the background showcases large glass doors, seamlessly connecting indoor and outdoor spaces amidst a verdant landscape.

5 out of 5 average rating, 17 reviews

Newly Built Private Home & Pool

Top guest favorite

An outdoor deck surrounds a circular swimming pool, complemented by a patio table and chairs. Several lounge chairs are arranged near the pool, and a large umbrella offers shade. Lush greenery borders the space, creating a private and serene environment.

Home in Saugerties

4.98 out of 5 average rating, 160 reviews

Spacious Staycation near HITS & the Hudson

Top guest favorite

An in-ground pool surrounded by a stone patio is visible, with clear blue water reflecting the sky. Green trees and shrubs are present in the background, enhancing the natural setting. Two lounge chairs are positioned nearby for relaxation.

Home in Germantown

4.98 out of 5 average rating, 58 reviews

Columbia County Farmhouse with Pool

Top guest favorite

A spacious outdoor deck surrounds a circular pool, featuring a clear blue surface and a ladder for easy access. A patio umbrella stands over a seating area with two chairs and a table, set against a backdrop of lush greenery and tall trees.

Home in Catskill

5 out of 5 average rating, 19 reviews

NEW! Catskill Family Hideout with Seasonal Pool

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, 65 reviews

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

A spacious backyard surrounds an inground swimming pool, with lounge chairs positioned nearby. Lush greenery and trees create a private atmosphere, while a blooming hydrangea bush adds a touch of color. A shaded area is provided by an umbrella over some seating.

Home in West Hurley

4.87 out of 5 average rating, 46 reviews

Hudson Valley Oasis with in-ground pool.

Condo rentals with a pool

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

4.87 out of 5 average rating, 86 reviews

Cozy Gem with Mountain Views

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

4.67 out of 5 average rating, 117 reviews

Windham Condo

A cozy living area features a light-colored sofa facing a decorative coffee table. A round rug with a nature motif complements the hardwood flooring. Large windows provide access to natural light, and a balcony can be glimpsed through the sliding glass door.

Condo in Windham

4.88 out of 5 average rating, 191 reviews

Cozy Mountain hideaway Windham, Hunter

A clear view of the community pool is presented, framed by a fence and surrounded by green grass. The backdrop features rolling hills and trees, with ski slopes visible in the distance. Lounge chairs are positioned near the pool, creating a relaxed outdoor setting.

Condo in Hunter

5 out of 5 average rating, 12 reviews

Mountain View Townhome w/ Community Pool!

A welcoming living area features a brown leather sofa with decorative pillows, a wooden coffee table, and a comfortable armchair. Soft lighting is provided by a floor lamp and a wall-mounted lamp. A sliding glass door leads to an outdoor deck surrounded by trees.

Condo in Windham

4.83 out of 5 average rating, 12 reviews

Windham-Hunter Lodge

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, 60 reviews

4 Bedroom Condo, Close to Golf Courses and Biking

A spacious outdoor balcony features black wooden chairs set against a backdrop of colorful autumn foliage. The heated pool and hot tubs are visible below, with the surrounding landscape showcasing a mix of greens and vibrant fall colors.

Condo in Windham

5 out of 5 average rating, 32 reviews

5-Star Lux Condo: Ski-In/Out, Heated Pool, Hot Tub

An outdoor area is shown featuring a heated swimming pool and two hot tubs surrounded by lounge chairs. The space is bordered by a landscaped lawn with neatly arranged trees and mountains visible in the background, creating a serene environment.

Condo in Windham

5 out of 5 average rating, 5 reviews

Luxury Ski in Ski out Condo + Amenities

Quick stats about vacation rentals with a pool in Windham

Total rentals
30 properties
Nightly prices starting at
ﺩ.ﺇ514 before taxes and fees
Total number of reviews
750 reviews
Family-friendly rentals
30 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi

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