Holiday rentals with a pool in Greene County

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 anyone craving calm. 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

Private lakefront home, hot tub & resort amenities

Stylish, and private Catskills lake-front house, w/ amazing lake views, a private hot tub, fire pit, kayaks, beach and dock; community swimming pools, tennis, pickle ball, basketball courts, baseball fields, playgrounds, dog beach & parks, golf driving range. This home has all you need to entertain, or work from. Located 2hrs from NYC, 15-30 minutes from Catskill, Hudson, Woodstock, Hunter and Windham ski resorts, the best restaurants, hiking, art galleries, antique shops, and cultural centers.

Little Farm Stay Catskill

Rustic first floor apartment on quiet, private horse farm. Private entry, suitable for single adult or couple. Great location at the foothills of the Catskill Mountains! 6 miles to HITS Saugerties, minutes from the village of Catskill and just a short ride to historical Woodstock. Enjoy hiking, bike trails and local shopping! Full Kitchen Bedroom: Queen, small single futon Living area: Cable TV & Foosball Table Back patio: seating, grill, hot tub and pool(seasonally) Fire pit Wi-Fi

Luxury Retreat | 6BDRM, Pool, Hot Tub & Movie Room

A private six-bedroom estate offering refined comfort and luxury. Nestled within the 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 maximum guest comfort, the home also includes a pool, movie room, premium sound system, and breathtaking mountain surroundings.

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.

Hudson River Sunset Getaway

With sunset views of the Hudson River and Catskill Mountains you can relax poolside during the summer months or enjoy the changing fall colors next to a cozy back yard bonfire in the fall. Located only 5 mins to downtown Hudson where you’ll find ample dining, drinking & shopping opportunities. Or head out to explore the Catskill Mountain Range only 30 mins away for the best hiking and skiing in the area. Sunset House is the perfect place for families or a couples getaway!

Cozy Gem with Mountain Views

A cozy apartment located less than a mile away from premier skiing and snowboarding at Hunter Mountain. Our place is located in a lovely community that has plenty of space to enjoy some quality time with family and friends. This is our home away from home and you can experience lot of personal touches throughout the apartment such as custom wood work, family photos and seasonal decoration. We can not wait for you to enjoy the beauty of Catskill mountains.

Only Ski In Out on Mtn | Hike, Golf, Fish, Relax

Mountainside 1 bedroom cabin that fits 4! Ski on/off Hunter Mountain right from your doorstep. Enjoy hiking within a 5-minute drive or walk right onto the mountain from your porch. 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.

Charming Lakefront Cabin with Hot Tub

Thoughtfully updated lakefront cabin, north of the Catskill mountains, in the Hudson Valley. Located inside the private, family-friendly Sleepy Hollow Lake community with guest access to pools, beach, tennis courts, & basketball (May-Sep). A peaceful retreat - come watch the hummingbirds from the porch or have your morning coffee looking out upon the lake! The cabin faces west over the lake so it's a wonderful spot to watch the sun set!

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!

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

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.