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Home rentals with a pool near Windham Mountain

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Top-rated rentals with a pool near Windham Mountain

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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.

A sparkling heated pool is framed by natural surroundings, with a stand-alone guest house visible in the background. Lush trees create a serene atmosphere, enhancing the privacy of the outdoor space. Nearby, seating areas and open grass provide inviting spots for relaxation.

Cottage in Bearsville

4.96 out of 5 average rating, 119 reviews

Contemporary Guesthouse with Private Heated Pool

Secluded studio on 13 acres in Bearsville with views of meadows, mountains and woods. Stand-alone guest house with queen size sleeping loft, kitchenette, fully tiled bathroom, elliptical trainer, and all amenities. Wake up in the morning and enjoy the amazing views with your coffee, hike in the woods, or meditate at the waterfall. In season enjoy the completely private heated pool. End the day with s'mores around the fire pit. An ideal getaway from the city yet only three miles to Woodstock.

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.

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.

Cabin in Shandaken

4.95 out of 5 average rating, 193 reviews

4BR Cabin w/ Hot Tub, Fire pit, Hiking, Pool (5/8)

*HEATED SALTWATER POOL OPENS MAY 8th* 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-mid Sept). Our newly added 6 person hot tub is available year round.

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 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.

A charming wooden studio cabin sits nestled among trees, surrounded by lush green grass. A set of steps leads to a private deck, furnished with a green umbrella, inviting guests to enjoy the serene outdoor views.

Home in Woodstock

4.91 out of 5 average rating, 199 reviews

Woodstock Romantic Mountain Studio w/ Pool

Come escape to the cozy Woodstock studio . Swim, hike, bike, BBQ and experience peace & serenity. Our large studio is a vacation gem and home away from home on 10 mountain top acres with large shared pool. 5 star. (Pool is shared with us, & we try to respect our guests privacy.) High-speed wifi Work remotely. The studio is on a private road just 5 mins from the center of Woodstock. Perfect for a couple, small family or single. 30 day rentals available October-May

Popular amenities for rentals with a pool near Windham Mountain

Free parking on premises

Air conditioning

House rentals with a pool

A private heated pool area is surrounded by a spacious patio, featuring lounge chairs and a shaded table. The red two-story cabin is visible in the background, with large windows and step access to the pool area. Lush greenery completes the inviting outdoor space.

Home in Stanfordville

4.96 out of 5 average rating, 48 reviews

Charming lakeside cabin with private heated pool

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

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

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

The outdoor space features a stone fire pit surrounded by a paved area, providing a cozy gathering spot. A fenced-in pool area is visible in the background, accompanied by lounge chairs, a gazebo, and a shaded dining area, all set against a natural green landscape.

Home in Saugerties

4.98 out of 5 average rating, 60 reviews

Upstate Family-Friendly House w/ Pool Pets Allowed

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

An outdoor swimming pool is surrounded by a spacious stone patio, featuring six lounge chairs in vibrant colors. Lush greenery and trees border the area, creating a private setting. The pool reflects the clear sky above, inviting for a refreshing swim.

Home in Kingston

4.83 out of 5 average rating, 70 reviews

Beaver | Pool, Firepit, Secluded, 10 acres

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

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

Other great vacation rentals near Windham Mountain

Top guest favorite

A private dock extends into the calm waters of Kinderhook Lake, surrounded by lush greenery. Soft clouds float in the sky, reflecting the tranquil atmosphere of the lakefront setting, while gentle ripples create a serene view.

Home in Valatie

5 out of 5 average rating, 111 reviews

Escape to Lakefront Leisure—Amazing views!

Top guest favorite

Home in Lake Katrine

4.95 out of 5 average rating, 111 reviews

Waterfront 3BR Home in Hudson Valley, Catskills

An outdoor deck is shown with a relaxing lounge area, featuring wooden chairs and a grill. A hot tub is positioned to one side, while a fire pit sits in the center. The serene lake view is framed by trees, creating a peaceful setting.

Chalet in Hunter

4.98 out of 5 average rating, 153 reviews

THE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE

A hammock hangs between two trees on a grassy area, inviting relaxation. The multi-level home features a wooden deck above, surrounded by lush greenery and trees. The exterior walls are a mix of wood and white, blending harmoniously with the natural setting.

Home in Hunter Mountain, Hunter

4.96 out of 5 average rating, 104 reviews

Private Mountain Lodge, 10mins to Hunter & Windham

Lush green mountains rise gently against a light blue sky, reflecting softly on the calm waters of a nearby lake. Dense trees line the shore, providing a natural border and a sense of serenity in the landscape.

Guesthouse in Windham

4.97 out of 5 average rating, 100 reviews

Little Bear’s Cottage Great location, cozy & cute

A small outdoor seating area features two metal chairs and a round table, surrounded by lush greenery. The view looks out onto a calm lake, partially obscured by foliage, creating a serene and private atmosphere.

Cottage in Red Hook

4.9 out of 5 average rating, 205 reviews

LAKE COTTAGE WITH HOT TUB - PAINTED TURTLE

A spacious wooden deck features a seating area with cozy chairs, a dining table, and an umbrella for shade. Potted plants adorn the space, and a grill is positioned nearby, creating an inviting area for outdoor gatherings.

Home in Woodstock

4.92 out of 5 average rating, 470 reviews

Mountain View Cottage - Sauna, Jacuzzi, Fire Place

Cabin in Shandaken

4.99 out of 5 average rating, 104 reviews

A Place Called Home in The Catskill

Quick stats about rentals with a pool near Windham Mountain

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

Destinations to explore