Home rentals with a pool near Windham Mountain

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open end of May - end of October. During the winter months we recommend soaking in our giant freestanding tub, which easily fits 2 humans.] Welcome to Maitopia - our modern, dog-friendly, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub, a floating fireplace and a heated pool in the summer. 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.

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.

Hideaway Windham/Hunter Fireplace, Snow & Skiing

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.

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.

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

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.

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..

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!

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.

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.

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!