Vacation rentals in Town of Gilboa

Modern Chalet w/Outdoor TV & Covered HOT TUB+POOL

Welcome to the beautiful Catskills! Our new beautiful A-Frame Chalet is situated on 6 acres of private forested land with lovely views of nature. Come stay in the fresh air! The chalet is fully stocked to be enjoyed for all seasons! Relax under the covered patio in all weather (rain or snow) in the HOT TUB or lounging on outdoor sectional while watching some NETFLIX/YOUTUBE TV all year round on our OUTDOOR TV, shoot a game of POOL in our upstairs Loft, or take a hike through our private TRAIL!!

Private 3BR escape w/ sweeping Mt Views & Firepit!

Click: "Show more" to read description before booking. NO PETS Perched high on a private road, The Ridge is a 3 BR / 2 bath newly constructed modern farmhouse w/ sweeping mountain views! Relax & dine outdoors on the wrap around deck & discover all of the comforts of home inside the open concept living space. Set on 5 mountainside acres, 3 min to Roxbury town & 10 min to wedding venues. Outdoor adventures await- 4 season activities at ski mountains, hiking, golf, farmers markets & culinary tours

Home Alone Mountain

Home Alone Mountain is a cozy cottage in a peaceful country setting. The house beautifully located in the small vacation community with a mountain view. Enjoy the privacy and tranquility of the 1,5 acre meadow adjacent to the state forest, take on the stroll in the woods, wander around the historic villages, take a swim in the pond, enjoy the open roads on a bicycle or visit Windham and Hunter villages. Find us on Instagrm @upstay z, #upstay z, #homealonemountain to learn more about the area.

Alpine Ridge - Mtn. Views, Fire Pit, Pizza Oven

Alpine Ridge is set on 3 acres of land, high up on a private road. From the house, you'll see the Bearpen Mountain Range across the valley. We designed and curated our home to be a perfect escape. Though remote, we are close to town for all the essentials: 5 mins to Prattsville, 15 mins from Windham and 25 mins from Hunter. The Catskills are abundant with hiking trails, ski slopes, quaint towns, local events, wedding venues, and farm-to-table restaurants. Follow us on IG: @alpineridgeny

Creekside Greek Revival Cottage

Newly restored 1840s Greek Revival cottage with new kitchen, two new bathrooms with showers (no tub) and new mechanical systems, two bedrooms, parking and vegetable and flower gardens with creek and horse pasture views. The house is furnished with 19th century antiques and decorative arts. Easily accessible to farmstands, antiquing, historic sites, restaurants and a nearby state park with an Olympic-size pool. The host lives next door, so help is available when needed, but privacy is allowed.

Chalet w/ Amazing Views on 22 Acres Near Windham

A nature-lover's oasis, this 3-bedroom/4-bed/2-bath log-built chalet with contemporary furnishings is perched high along the northernmost edge of the Catskill Mountains offering unforgettable panoramic views from inside and out across 22+ secluded acres. Due to its proximity to hiking trails, lakes, rivers, breweries and wineries as well as Windam (7 mi), Hunter (16 mi), Catskill (26 mi) and Hudson (29 mi), this is the ideal location from which to explore the best the Catskills has to offer.

Catskills Retreat - hot tub, views, summer avails

This private, light-filled cabin on 3.5 acres in Gilboa, NY is a perfect secluded retreat for adventurers, families, or groups of friends. Relax while grilling out on the large deck with great mountain views, then start a fire in the wood burner or fire pit, or enjoy the sunset from the hot tub! The cabin is located near Hunter, Windham, and Plattekill ski areas, as wells as Minekill State Park and the Catskill Scenic Trail, and various wedding venues making it a perfect weekend getaway!

Spacious cabin w/grill, firepit & mountain views

NOTE: Click “Show More” to read the full description. Home with stunning views perfectly situated between Roxbury and Stamford! Drink your morning coffee at the bar on the deck overlooking the mountains, curl up with a good book in the reading nook, or explore the farms, mountains, and countryside of the beautiful Western Catskills. Cabin is situated on five beautiful acres at the end of a private drive. Beautiful sunrises over the mountains, with wide-open stargazing after dark.

Mountain and tree view cabin on 12 private acres

A great escape awaits you on 12 acres of private land. If you prefer a relaxing vacation or if you want to get involved in local activities (hiking, biking, swimming, skiing, snowshoeing, sledding), this is your place. Enjoy 360 degree views of the Catskill Mountains from almost anywhere on the property. Sip your morning coffee while watching the sunrise on the large deck. Play in the large private yard. Clear evenings are the best for sunsets, a fire pit and star gazing.

Mountains Views & Private Stream

Enjoy incredible mountain views at this 4 bedroom, 2 bathroom retreat in the heart of the Catskills Mountains. Home to Gilboa’s Fossil Museum and a short drive to scenic Belleayre, Windham, and Hunter mountains, this ideal secluded oasis sits on 5 acres of gorgeous landscape with a babbling brook. Nearby attractions include Minekill Falls and the Pakatakan Farmer’s Market. Look no further for adventure in serenity. We would love to host your next escape to the mountains.

Great for hunters-skiers-hikers close to Windham

The quiet tranquility of mountain nature. Minutes from the Windham mountain ski resort. State land nearby for hunters as well. This one bedroom home has key pad entry, a full kitchen, dining area, living room, front deck, spacious rear deck, fire pit, acres of back yard, full bathroom, can sleep four with queen size bed and pull out couch, wifi, fire stick tv. All the comforts of home. This is a fully furnished one bedroom home that was recently converted to an Air BNB.

Fern Valley Eco-Cabin

Get away from it all in this secluded off-grid cabin. Inspired by traditional lean-tos and modern Swedish design. This minimal space features a wall of windows that makes you feel like you are sleeping in the trees, while staying cozy and dry! Use this as a base camp to explore the Catskills, or just relax, unplug, and listen to the nearby stream, birds, & the rustle of leaves! *For winter bookings please fully read the Other things to note" section*