Home rentals with a pool near Windham Mountain

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Top-rated rentals with a pool near Windham Mountain

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

A striking landscape features a modern home beside a serene pond. Lush green lawns and colorful trees reflect beautifully in the water. Towering conifers and deciduous trees frame the scene, enhancing the idyllic outdoor setting.

Home in Woodstock

4.94 out of 5 average rating, 398 reviews

Woodstock Historic Artist Estate - The Pond House

Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

Guest favorite

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

4.94 out of 5 average rating, 156 reviews

StunningViews•Bright2BR•Pool•NearFarm•Lakes•Farm

A quiet mountain hideaway where the air feels soft and clean, and the view from the deck slows your whole spirit down. This cozy 2BR retreat sits between Windham and Hunter—perfect for families, solo wanderers, and ski seasonal deals. Fast WiFi, a full kitchen, and short stays on selected days make it easy to escape, breathe, rest, and reconnect with yourself. Easy drive to charming little towns - Windham, Hunter , Tannersville . Swimming pool on premises , CD Lane Lake with beach and free boat

Guest favorite

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, 178 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.

Guest favorite

Home in Windham

4.95 out of 5 average rating, 108 reviews

Catskill Villa | 6BDRM, Pool, Hot Tub & Movie Room

A spectacular six-bedroom estate offering refined luxury and comfort. Nestled within the exclusive Dingley Dell Estate, it's just a six-minute drive to Windham town and about 25 minutes from Hunter Ski Resort. The property features expansive, beautifully landscaped grounds, inviting outdoor seating areas, a prime location, and exceptional privacy. Completely renovated for ultimate guest comfort, the home also includes a pool, movie room, premium sound system, and breathtaking mountain views.

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, 136 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 usually summer and winter. Air Conditioning in summer.

Guest favorite

The expansive outdoor space showcases a vibrant green lawn framed by trees and gentle hills. In the distance, the mountainous terrain presents a picturesque backdrop under a clear blue sky, with sunlight illuminating the landscape. Outdoor grills are partially visible in the foreground.

Townhouse in Hunter

4.9 out of 5 average rating, 105 reviews

Hunter Mountain Retreat | Views, Pool & Fireplace

Enjoy the BEST LOCATION IN THE CATSKILLS with Scribner's Lodge right next door, Hunter Mountain 1 mile away, Tannersville a town over, Windham mountain 7 miles away, hiking, lakes, restaurants and breweries all around! Amazing 4 bedroom, 3 bathroom townhome with unbeatable views of Hunter Mountain. Stocked with all the essentials, multiple fireplaces, outdoor grill and a new patio! Bring your skis and snowshoes or rent skates for the winter and enjoy the shared outdoor pool in the summer.

Superhost

Chalet in Jewett

4.97 out of 5 average rating, 193 reviews

Secluded Catskills Retreat w/ Hot Tub & Views

Escape to a renovated Catskills country home with modern comforts and classic charm—perfect for a relaxing getaway or outdoor adventure. Nestled in the heart of the Catskills, this retreat is just minutes from Hunter Mountain, Windham Mountain, and Kaaterskill Falls, with endless opportunities for skiing, hiking, swimming, and exploring. The home features a fenced-in yard, a stocked kitchen, and modern amenities. After a day outdoors, unwind by the firepit or soak in the hot tub.

Superhost

A spacious outdoor deck is visible, furnished with a round table surrounded by several chairs and a lantern on top. A comfortable seating area with a couch is positioned nearby, set against a backdrop of lush greenery.

Condo in Windham

4.69 out of 5 average rating, 127 reviews

Windham Condo

This condo is right off Route 23, minutes from Windham Mountain. Head to the Catskills. The complex has a pool, tennis, pickleball & basketball 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. Your place to enjoy all the hiking, mountain biking, and golf Windham has to offer. Only 2.7 miles from Windham Mountain Resort. Guest ID may be required on arrival.

Guest favorite

A game room features a pool table, shuffleboard table, and comfortable seating. Large windows allow natural light to fill the space, highlighting rich wood accents and green walls. Access to the outdoor area is provided through glass doors, complementing the recreational atmosphere.

Villa in Cornwallville

4.95 out of 5 average rating, 104 reviews

Catskills Retreat-Pool, Hottub, Bar, Shuffleboard

Welcome to Blue Heaven! A true paradise retreat with 2 houses, your own private inground pool, outdoor shower, pool house, playground, a Speakeasy bar room with billiards, darts, and shuffleboard! Located in the heart of the Catskills just 3 minutes away from Zoom Flume water park and 15-20 minutes away from Hunter/Windham Mountains. Enjoy swimming, roasting smores in the firepit, hiking, skiing/snowboarding, snowshoeing, or soaking up the stars in our hot tub.

Superhost

The image features a modern hot tub in the foreground, with bubbling water and a clear dome structure nearby. The dome showcases a seating area surrounded by nature, with trees visible in the background against a bright blue sky.

Chalet in Prattsville

4.9 out of 5 average rating, 131 reviews

White Holiday Cozy Chalet Pool/Hot Tub/bubble room

⛰️This private modern haven is the place to be to take a break from our everyday busy lives and get away from it all. Enjoy a relaxing soak in the hot tub while indulging yourself with a glass of fine wine. The space is designed for family & friends to get together, have a good time, and enjoy each others company. Activities include hiking in the summer, skiing in the winter, barbeque and fresh air all year round!

Guest favorite

A welcoming living area features a stone fireplace and wood-beamed ceiling. Two comfortable armchairs and a sofa are arranged around a circular coffee table. Large windows, framed by sheer curtains, allow natural light to brighten the space. A television is mounted on the wall, enhancing the cozy atmosphere.

Townhouse in Windham

4.97 out of 5 average rating, 109 reviews

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

A cozy townhouse 3 bdrm /2.5 bath in the center of the Catskills (Windham Mountain Village), this retreat is perfect for families, celebratory events or just a quiet nature getaway. From wineries to breweries, to zip lining and hiking, to admiring the many waterfalls, this area has something for everyone! PLEASE NOTE: POOL AND HOT TUB WILL BE CLOSED FROM SEPTEMBER 2 to NOVEMBER 27, 2025

Superhost

A seasonal saltwater pool is surrounded by a wooden deck and lounge chairs, offering a scenic view of the lush hillside. An umbrella provides shade, and a basketball hoop is positioned at one end of the pool, enhancing outdoor leisure options.

Cabin in Town of Shandaken

4.95 out of 5 average rating, 247 reviews

Catskills Retreat | Heated Pool & Hot Tub

Tucked away in the Catskill Mountains, our private cabin feels like you’re a world away while still being just minutes from hiking, restaurants, skiing, and charming mountain towns. It’s one of those places where mornings start with coffee surrounded by nature, afternoons are spent by the pool, and evenings end in the hot tub or around the fire pit under the stars.