Vacation rentals in Town of Gilboa

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Top-rated vacation rentals in Town of Gilboa

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

A charming cottage is visible surrounded by vibrant autumn foliage, set on a spacious green lawn. A decorative clock and fence in the foreground frame the scene, while a front porch invites relaxation. Adjoining trees enhance the secluded, tranquil atmosphere of the property.

Cabin in Town of Gilboa

Windham Cabin Secluded With Bonus Mini A Frame

Less than two hours and forty-five minutes from NYC, twenty minutes from Windham Mountain, & 10 minutes from Mine Kill Park. Enjoy four seasons of mountain fun in the Catskills. Wake up to a breathtaking sunrise over the mountains and absorb the serenity of our secluded property that borders wooded state land. This house is perfect for couples or a family with children, with a queen-sized bed in the master bedroom, daybed with twin mattress in the spare room, & a pullout sofa in the living room.

4.91 out of 5 average rating, 196 reviews

Top guest favorite

A serene landscape is presented with rolling green hills under a clear blue sky. The glowing sun rises on the horizon, illuminating the dewy grass and trees. Fenced areas and distant hills contribute to the peaceful atmosphere of the mountain top.

Farm stay in Conesville

6 Bedroom 1860 Farmhouse Mountain Views Windham

Near Windham! Take time away from it all to enjoy a beautifully situated private farm on a 150- acre mountain top. Favorite things to experience are exploring the wilderness, waterfalls, farm animals, the sunrise from the front porch, the sunset view from the upper mountain field, collecting eggs, skiing, snowshoeing, cross country skiing, sledding, Lake access at Huyck Preserve (kayak, swimming hiking, picnics), cooking farm fresh meals (farm to table ingredients by the season). Exquisite stars

4.99 out of 5 average rating, 107 reviews

Top guest favorite

The loft area features wooden walls and ceilings, accentuating the natural log construction. A gray sofa with yellow accent pillows is positioned alongside a low black coffee table. Large windows provide a view of the surrounding landscape, while a geometric-patterned rug adds warmth to the space.

Chalet in Town of Gilboa

Luxurious Chalet w/ Incredible Views on 20+ Acres

A nature-lover's oasis, this 4 bed/3-bedroom/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 20+ 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.

4.98 out of 5 average rating, 209 reviews

Guest favorite

Cabin in Town of Gilboa

Cozy Pet-Friendly Cabin w/GameRoom and FirePit!

Welcome to Black Birch Lodge - tucked away on 18 private acres in the Northern Catskills. Our home is perfect for group & family getaways. We're close to skiing, hiking, wedding venues and the quaint towns of Stamford & Roxbury. Please note our home is located in a natural mountain environment. While we clean thoroughly between guests, occasional bugs or wildlife sightings are normal in this setting. This is part of the charm of staying in nature and differs from a hotel or city property.

4.97 out of 5 average rating, 111 reviews

Superhost

A covered outdoor seating area features a sectional sofa alongside several colorful Adirondack chairs on a patterned rug. Decorative string lights are draped overhead, and firewood is stacked nearby, creating a cozy space for relaxation.

Chalet in Town of Gilboa

Modern Chalet w/Cedar SAUNA, HOT TUB & Outdoor TV!

Welcome to the beautiful Catskills! Our 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 the HOT TUB or lounging on outdoor sectional while watching some NETFLIX/YOUTUBE TV all year round on our OUTDOOR TV, enjoy the brand new SAUNA (March 2026) shoot a game of POOL in our Loft, or take a hike through our private TRAIL!!

4.89 out of 5 average rating, 132 reviews

Top guest favorite

A cozy cabin is illuminated at night, surrounded by string lights that outline its exterior. A fire pit is situated in the foreground, with guests gathered around. The expansive deck is partially visible, enhancing the inviting atmosphere of the outdoor space.

Cabin in Town of Gilboa

Catskills Cabin with hot tub and dog run!

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 well as Minekill State Park and the Catskill Scenic Trail, and various wedding venues, making it a perfect weekend getaway!

4.9 out of 5 average rating, 205 reviews

Top guest favorite

A cozy outdoor space features comfortable seating and a modern fireplace, set against a stunning backdrop of lush trees and a colorful sunset. A hot tub is visible nearby, inviting relaxation. Soft lighting adds a warm touch to the tranquil atmosphere.

Home in Lexington

Valley View Chalet: AC, Hot Tub, Firepit, Games

Spacious, peaceful lux cabin atop the Catskills. Enjoy mountain views and soak in the hot tub. Catch up in the vaulted room by the stone fireplace w/ a wide game selection, with a 2nd living room downstairs. Host a dinner party with our fully equipped kitchen. 20 mins to 6 towns. Visit breweries, antique shops, dine, hike, fish, golf, or relax. Great for groups, families, kids & pets. Fast 600mb internet, AC, EV charger, generator. WFH, newborn, pet friendly. 3+ nights get discounted rate

4.99 out of 5 average rating, 169 reviews

Guest favorite

The A-frame cabin is framed by vibrant autumn foliage, featuring warm lighting that highlights its contemporary exterior design. A spacious wooden deck is furnished with seating and a dining area, overlooking a manicured lawn. The surrounding trees display a palette of orange and yellow leaves.

Cabin in Stamford

The A-Frame at Harvest Moon Acres

Escape to this cozy, pet friendly Aframe tucked in the mountains - perfect for a peaceful getaway surrounded by nature with fireplace and mountain views in Stamford, NY, where the beauty of the Catskill Mountains surrounds you. Whether you’re sipping coffee by the fire, exploring nearby trails, or unwinding under the stars, the cabin is designed for comfort, relaxation and a little adventure Close to scenic hiking trails and nature spots. Short drive to local coffee shop and cafe.

4.97 out of 5 average rating, 328 reviews

Top guest favorite

A modern cabin is situated on a hillside, showcasing a spacious deck with seating and string lights. The structure features large glass windows, allowing a view of the surrounding forest. A cozy fire pit is visible on the grass, inviting outdoor gatherings.

Chalet in Stamford

Spacious cabin w/mountain views & woodstove

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.

4.93 out of 5 average rating, 170 reviews

Guest favorite

A vibrant red barn is set against a backdrop of rolling green fields and colorful autumn foliage. The surrounding trees display shades of orange, yellow, and green, while distant mountains rise under a clear blue sky.

Home in Town of Gilboa

Mountain 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.

4.94 out of 5 average rating, 155 reviews

Top guest favorite

Home in Prattsville

Catskills Retreat - Game Room, Hot Tub, EV charger

Welcome to our Mountain Chalet. Bring the whole family to this spacious retreat with plenty of room for fun and relaxation.This specious house, nestled on 2.5 acres, features 4 bedrooms, 3 full bathrooms, Hot Spring hot tub, a game room, a cozy gas fireplace, smart TVs, an EV charger and more. It has beautiful views. Located in the heart of the Catskills, 15 min from Windham Mountain, 20-25 min from Hunter and 40 min from Belleayre. Your perfect mountain getaway awaits!

4.97 out of 5 average rating, 106 reviews

Guest favorite

A single-story home is set among trees, featuring a front porch with a wooden railing. A gravel driveway leads to the entrance, framed by a landscaped area. The surroundings include additional structures and a green landscape, providing a peaceful natural setting.

Home in Town of Gilboa

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 two 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.

4.85 out of 5 average rating, 197 reviews