Family-Friendly rentals near Windham Mountain

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.

Unique Tiny House Glamping in the Catskills

Looking for the perfectly romantic glamping getaway? This stunning handcrafted hut was designed by my Buddhist mother for a meditation retreat, and to commune with nature. With unique timbered walls and ceilings, a wood-burning stove (the only heat source), rustic stone detailing on the walls and large glass windows, you'll feel like you're living in the woods, but with the comfort of the indoors. Please note that this is an off-grid camping cabin without water, but there is electricity.

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 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.

Studio 3 BEDS-SLEEP 4

Light-filled studio in downtown Windham. Beautiful mountain views from your balcony; at night gaze at the moon & stars If you want solitude, this is the place to be! Daytime, take a walk down to the river & enjoy! Walking distance to restaurants & small grocery. Studio is big, with closet, full bathroom, well-stocked coffee area with microwave and refrigerator. Maximum 3 people; 1 double & 2 twins. Check-in: From 4PM off-street parking, Free Wifi /Basic Cable /Linens/Coffee

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.

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. Air Conditioning in summer.

5 Min to Skiing | Hot Tub | Fire Pit | Pool Table

Escape to this newly renovated mountain cabin just 5 minutes from Windham Mountain ski resort! With a private fishing pond and a deck offering panoramic resort views, it's a perfect outdoor retreat. Inside, enjoy a pool table, Pac-Man arcade, and shuffleboard for endless fun. A 2-minute drive to town makes dining and shopping convenient. The cabin's modern amenities, cozy fireplace, outdoor firepit, and hot tub guarantee a comfortable and relaxing stay.

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.

Cozy Cabin Condo by the Mountain, 5mins to skiing!

Steps from the Mountain! Just 1 mile away with a crisp mountain view, our beautiful chalet is a mere 5 minute drive from the slopes of Windham and just 15 minutes from Hunter! A short walk or drive from the charming town of Windham, you're perfectly located for a country getaway. The town itself is a wonderful mountain community with many great shops, restaurants and activities all within a short drive.

Cozy clean apt 5 min Hunter/ Windham ~ Dog Heaven

Take a break and unwind at this peaceful oasis. Hunter Mtn is 5 min away & Windham 10 min for those who want to hit the trails, restaurants, bars then retreat to a quiet place at the end of the day. You’ll have access to 4 acres of land and East Kill Creek. Great for dogs and trout fishing. Thank you for looking. Yes we have A/C.

Trendy Condo Hunter Mountain

Newly renovated modern condo slope-side at Hunter mountain. Come enjoy the beauty of the Catskills & winter events while staying at our cozy and stylish condo. Warm up by the electric fireplace, fix a meal and have a drink in our brand new kitchen, watch a movie, and enjoy a restful sleep in a relaxing bedroom.