Holiday rentals in Town of Ashland

Custom Catskills private retreat

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 :)

10acres Catskill Mntn vws, hot tub, fire pit, pond

Get away to this beautiful remote location in the Catskills region. Stunning views of mountains and over 10 acres of land to explore. Located on the property is a hot tub, fire pit and a serene pond where you can just sit back and take in the views. We are about a 15 minute drive away from Windham Mountains ski resort, 13 minutes to Bearpen Mountain Sports, less than 30 minutes to Hunter Mountain and less than 40 minutes to Kaaterskill Falls (the most famous Catskill Mountain waterfall).

Sauna|Hot tub|Hunter Mountain View|Chef's kitchen

Escape to Le Chalet, your private modern luxury retreat in the heart of the Catskills, just 2.5 hours north of NYC. Located near multiple ski resorts (Windham, Hunter, Bellaeyre), scenic hiking trails, and fishing streams, this stylish designer space features breathtaking Mountain views, Chef's kitchen, and beautifully curated Outdoor spaces, perfect for relaxation. Relax in the cedar barrel sauna with a panoramic window, stargaze in the hot tub, and roast marshmallows by the firepit.

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.

Casa Magda - Designer Home near Hiking + Swimming

Relax and recharge at Casa Magda—a design-inspiring home on 9 acres in Windham, NY—just 2.5 hrs north of NYC! For design lovers and nature seekers, this 1980s gem has been redesigned with modern flair and offers serene solitude. Relax by the hot tub, cozy up by the fireplace with a record and lounge around the campfire to view stellar constellations and the Milky Way. Explore nearby eateries and hikes. Ski the Windham slopes within a 7 min drive, or head to Hunter in 15 mins.

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

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.

Private Catskill Getaway | HotTub w/ Mountain View

Your perfect leaf peeping getaway to the Catskills!!! Escape the busyness of life and unwind at The Catskills Mountain House — a cozy, private cabin getaway on 8 wooded acres with breathtaking mountain views from the hot tub. Come relax, reconnect, and return home renewed!! Perfect for birthdays, proposals, anniversaries, honeymoons, or just quality time together. Follow us @ thecatskillsmountainhouse for local recs

Original Windham Farmhouse

Direct mountain views and 1 mile to mountain or downtown. Set high-up for privacy, the house has an open concept kitchen/dining and living room. Original timber beams are cozy next to the large gas fireplace. Huge basement recreation room with adjoining bunk room and bath for the kids. SmartTVs, perfect for multiple families, couples or friends. Wander the 10 acre backyard.