House holiday rentals in Windham

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.

Wow! Panoramic Mountain View, Minutes to Windham!

This pristinely-kept vacation home has endless mountain views on rolling country acres. Come and stay just to get away, enjoy both the sunrise and sunset views from the expansive deck. Curl up by the wood burning fireplace or the outdoor fire-pit, or take a sunset plunge in our backyard hottub and enjoy the picturesque views of Windham, NY from across the valley. A serene 8 mile drive will take you into the historic Town of Windham, NY to enjoy a day of skiing, site-seeing, hiking or dining

Scandi A-Frame w/Hot Tub & Sauna

Escape to Wilderkaat {WILL-der-cat} ⮕ NEW GUT RENO 3-bed 2-bath Scandinavian modern A-frame chalet ⮕ 2 private wooded acres ~10 miles to Hunter & Windham ⮕ 8-person hot tub, cold plunge tub, 6-person barrel sauna ⮕ Backyard firepit w/Adirondack chairs & string lights ⮕ Outdoor games: bocce cornhole horseshoes disc golf ⮕ Fully stocked open kitchen, Weber grill, in & outdoor dining for 8 ⮕ Smart TVs & Sonos throughout, high-speed fiber WiFi ⮕ A Catskills perfect blend of relaxation & adventure

Private Waterfall Retreat on 10 acres

Newly renovated 2 BR private home in the Catskill foothills perched next to a beautiful waterfall and stream. Furnished with quality and care, with an eye toward modern style and comfort. Gas Grill on covered porch, Campfire area, & outdoor table and benches for dining outside! Hiking trails and swimming holes nearby. Walking distance to Zoom Flume Waterpark, 12 mile drive to Windham Mountain, 30 minutes to Hudson. But really no need to go anywhere once you settle in to this quiet retreat!

Serendipity Lake House on Lake Heloise

Escape to Serendipity — your private lakefront sanctuary in the Catskills, perfect for ski getaways, family retreats, special events, and nature lover's paradise. Unwind in a 4,000 sq ft lodge with cathedral ceilings, a lakeside deck, hot tub, fire pit, boating, and fishing access — all on 9.5 acres of breathtaking scenery. Just minutes from skiing, hiking, and fall foliage drives, this is the ultimate all-season destination. House sleep 14 people with room for more. Over 14 people $60/person.

Spring in style @ Killercat Mountain House

Natural splendor meets seductive style at #killercatmountainhouse, a design-focused retreat 5 minutes from Hunter Mountain—and 13 minutes to Windham Mountain—that delivers a fresh & colorful Catskills experience. Embrace spring from our expansive deck, hot-barrel sauna, fire pit & roomy hot tub, or unwind by the fireplace w/records & games. Our Parisian-chic décor provides Insta-worthy moments inside & out, while our epic views & amenities allow outdoor enthusiasts to indulge all season long.

Private cabin in the Catskills

This is a 2 bedroom 1 bath house located just 7 minutes from the Windham ski mountain. The house is surrounded by scenic land with few neighbors to be seen. Skiing, fall foliage, swimming holes, hiking, golf, antiquing, horseback riding, local farms are just a few things to name that this area has to offer. The house itself is a true retreat, you will leave totally re-charged - sweet air, bird chirping, star gazing, grilling, bong fire or simply enjoy a few days of not seeing another soul :)

Valley View Chalet: AC, Hot Tub, Firepit, Games

Spacious, peaceful lux cabin atop the Catskills. Enjoy mountain views and soak in the hot tub. Catch up in the vaulted room by the stone fireplace w/ a wide game selection, with a 2nd living room downstairs. Host a dinner party with our fully equipped kitchen. 20 mins to 6 towns. Visit breweries, antique shops, dine, hike, fish, golf, or relax. Great for groups, families, kids & pets. Fast 600mb internet, AC, EV charger, generator. WFH, newborn, pet friendly. 3+ nights get discounted rate

Modern House with Mountain View @Getawind

Experience luxury and comfort in our newly built property. Marvel at the breathtaking panoramic views of Rusk mountain through floor-to-ceiling windows. Unwind in the sauna or hot tub, and gather around the fire pit for cozy evenings. Enjoy outdoor movie nights with our projector, or savor grilled delights in the patio area. Warm up by the fireplace, explore Ski resorts, Golf Clubs and more. It's the perfect retreat for families and friends. Book now and create unforgettable memories!

Chalet with HotTub 5 min to Windham, 15 min Hunter

Cozy Chalet style house nestled in a quiet spot and 5 minutes to Windham Mountain and close to hiking trails 15 minutes to Hunter Mountain 40 minutes to Belleayre Mountain. Relax by the fireplace after skiing TV with Netflix, Amazon and Hulu. Confortable couch with a equipped kitchen With 3 bedrooms. This property has a beautiful yard. Fairly private yet close to everything. Supermarket and restaurants near by (5 min by car) 15 min. to Colgate Lake 25 min. to Kaaterskill Falls

Creekside Couple's Retreat w/Hot tub, Sauna & More

Tucked by an enchanting creek, this newly built cabin is a serene haven where nature and comfort meet. Unwind together in the hot tub beneath the stars, relax in the wood fired sauna, or enjoy a fun evening in the game room. Let the soothing sounds of the creek lull you to sleep as you take in the beauty of the outdoors from every window. Explore nearby trails, quaint towns, and secret escapes. Pet-friendly, perfect for couples seeking a magical retreat in every season.

Big Red Retreat 3 min to Windham Mountain & Golf!

Welcome to Big Red – Your Ultimate Mountain Retreat! Nestled in the heart of the scenic Windham area, Big Red invites you to experience the perfect blend of comfort, convenience, and adventure. Whether you're here to hit the slopes at Windham Mountain, explore the tranquil Windham Path, or tee off at the nearby golf course, our spacious 6-bedroom, 2.5-bath home is your ideal basecamp for an unforgettable getaway.