Family-friendly vacation rentals in Windham

Lothbrok - the "B" side - 2 mile slopes & town

5 min to Windham Mountain / easy 15-19 min to Hunter! 1 mile to Windham's Main Street - restaurants, pubs, movie theatre & shopping. Remodeled with luxury vinyl flooring, low VOC paint, LED lighting, Culligan water treatment, excellent cell phone service & FREE WiFi means no issues making calls/texts/internet. We kept some of the groovy charm of the 1970's (spiral stairs) and brought the house into this century looking brand new again. NOT SAFE for babies, children under 12 or pets. No smoking.

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.

Diamond Notch - Mini A-frame, Spectacular Views

+ Amazing Views + Very Private + Modern Design + Indoor Propane Fireplace + Deck w/ String Lights, Chairs + Sun Shade + Charcoal BBQ + Wood Solo + Camping Stove + Star Gazing The Diamond Notch is a site-specific, passive-house level insulated, off-grid mini A-frame - locally designed & built in co-op w/ Lexington Arts + Science Requires a 5+ min hike in. Bring hiking boots. Micro spikes provided for the uncleared snowy trail. We provide bedding + fresh linens (No T mobile reception)

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.

Little Red Cabin Near Windham & Hunter w/ Hot Tub

Nestled in the woods, our 3 bedroom cabin offers the perfect escape from the hustle and bustle of everyday life. The cozy interior features a warm, inviting atmosphere with all the amenities you need for a comfortable stay. The spacious living room is the perfect place to unwind after a long day of exploring the great outdoors, complete with a cozy fireplace and outdoor hot tub that offer stunning views of the surrounding landscape. Follow us on IG @thelittleredcabinny

The 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.

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.

"Your Country Getaway at Beulah Land Farm."

Enjoy a one bedroom apartment with a private entrance. Head up the old rear staircase around the back of a quaint 100 year old farmhouse. Stairs are a little steep. There is a kitchenette with a two burner stove, sink and under counter fridge. There is one full bath with a shower stall. In the living area there is a day bed with an extra twin mattress underneath. There is wireless internet for your use as well. It is 25 minutes to ski areas.

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.

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.