Family-friendly rentals near Windham Mountain

Beautiful Windham Ski/Summer House

A spacious 4 bedroom house located in Windham, NY just 5 minutes from the mountain. Built in 2012. Brand new comfy couches just purchased March 2021. Beautifully decorated with large wood doors, stone fireplace, and granite countertops. Wake up to view of the slopes from the large windows. Truly breathtaking views year round. Four bedrooms three with queen beds and 1 with a bunk beds (full size beds/twin trundle on the bottom). Plus a couch located in the loft area. The house sleeps 12. Full basement with television and couch with a ping pong table, a basketball game and a fooseball table. There are 3 full bathrooms along with one half. The main floor has a fire place along with tv and a full kitchen and dining area all with full views of Windham mountain. Come see the leaves turn and enjoy Great hiking, biking, golf and skiing when the snow comes. One mile from town and Windham Mountain. Pricing for a week goes from Friday to Friday. Renters must be at least 25 years old. Please no pets are allowed at the house, this is a strict policy no exceptions. No parties allowed Cleaning fee additional Christmas and New Years week have a 4 day min. and MLK and Presidents day week have a 3 day min.

"THE PAINTED COW" 5 acre farm in the mountains!!

"Come to nature" ALL FOUR SEASONS at our lovely renovated 1900s farmhouse set on 5 acres one mile from Windham Mountain Club. This vacation rental is perfectly suited for multi-family and friend getaways. Highlights: original artwork throughout, large country kitchen, cozy open bunk cove for kids, laptop workspaces. Outside: Starry skies, walking distance to Main St, wraparound porch, cozy evenings around the fire pit. Let the dogs and kids just run or cruise the Toboggan Hill on a snowy day.

Hidden Catskills Cabin • Private Trails • River • Swim Hole

Tucked away between Windham and Hunter, this cozy 3-bedroom cabin feels like your own secret mountain hideaway. Perfect for couples or small groups looking for a quiet Catskills escape. Mornings are slow, coffee tastes better here, and nights are for laughter, stories, and starry skies. Whether you’re hiking, or simply unwinding, this cabin offers that rare mix of warmth, comfort, and true Catskills magic. Outdoor enthusiasts heaven. River access through private trail . Epic summer vacation !

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 :)

Windham Manor | 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.

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.

Lux Hunter Mountain Retreat | Sauna + Game Room

NEW ♨️ Private Sauna + Family Game Room! Escape to our beautifully remodeled 3BR/2BA mountain retreat set on 6 private acres in Jewett. Relax in your private indoor sauna or enjoy the game room with arcade, foosball, and darts. 📍 ~10 minutes to Hunter & Windham Mountains 📍 ~2.5 hours from NYC — an easy year-round getaway Ski, hike, bike, swim, golf, fish, explore local vineyards, or dine out — all within 10 minutes. Then return to comfort, space, and peaceful mountain surroundings.

CozyCatskillChalet w/ Hot Tub (Catskill Mountains)

At face value, IG: @cozycatskillchalet appears to be just a humble little getaway tucked in the Catksill Mountains of Windham, NY. But even the most discerning guests will be quickly spirited away by the rustic charm and postcard-eqsue surroundings all around. At night, can't-be-beat stargazing on the back deck (or while soaking in the hot tub) will have you convinced this humble hideaway is a lot more illustrious than it lets on. Disclaimer: The chalet is not a luxury hotel or property.

Luxe Lodge w/ Mt View | Hot Tub, Fire Pit, Game Rm

Plan your all-seasons escape to this beautiful, luxury chalet with direct views of Windham Mt., just a 5 minute drive to the slopes. Situated at the end of a private road on 3+ acres, enjoy this mountain getaway's hot tub, oversized deck, pond, firepit, huge game room, and other modern amenities. Just 2.5 hours from NYC, and minutes away to skiing (<5 min to Windham Mtn, 15 min to Hunter Mtn, 40 min to Belleayre Mtn), hiking, biking, swimming, golfing, fishing, vineyards and restaurants!

Alpine Chalet on Spectacular Property

Inspired by their travels in the Swiss Alps, the hosts of the Mountaintop Chalet invite guests to their peaceful alpine guesthouse atop a mountain in the Northern Catskills. Nestled on a quiet, private road, the Mountaintop Chalet is just an 8 minutes drive to downtown Windham, NY, 10 minutes to Windham Mountain and 18 minutes to Hunter Mountain. This tranquil yet accessible setting makes it the perfect escape for couples, families and friends. Follow on Insta at mountaintop_chalet.

Cozy Creekside Cabin | 5 Mins to Windham Mt!

Nestled in the hills of Windham NY, the Creekside Cabin is a hidden gem just under 2.5 hours from NYC. Ideal for families and small groups of friends, this cozy cabin features three bedrooms, one bathroom, a comfortable living room overlooking a tranquil creek, and a fully equipped kitchen with a wood-burning fireplace. Whether you're looking for a weekend escape or a longer retreat, the Creekside Cabin offers a peaceful and relaxing stay in a beautiful natural setting.

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.