Vacation rentals in Shawangunk

Garden View Guest Cottage

Located under 15 min. to Stewart Airport...1 mile to City Winery , nearby Angry Orchards , 1/2 hour to West Point Charming cottage setting located in the village of Montgomery, NY, Come for the day or stay for a few to take in all this historic area has to offer. Walk to some of the best restaurants in Orange County or simply read a book in the gardens... Truly a great value since it's a true "apartment " like setting..not just a room, with all the conveniences and sleeps up to 6 people

Hudson Valley Tiny House

If you've been looking for the tiny house experience, look no further. Michelle and Chris built this tiny house to live as eco-friendly, comfy, and healthy as possible. Built with only non-toxic and all natural materials with a state of the art fresh-air system. Two heating systems for the winter. Enjoy wildlife or relaxing at the river bend on our 5-acre property or explore the awesome attractions close by: winery, New Paltz downtown, “gunks” rock climbing, Minnewaska State Park, and more!

School Bus Glamp w/HotTub~15min to Gunks/New Paltz

Experience a unique stay in a magic school bus on 10 acres! 15min to Gunks, New Paltz, Angry Orchard HQ, Minnewaska &more! Relax in the hot tub in the morning or sit under the stars at night. Two beds; twin & full w/bedding. Heater, electric blanket, mini-fridge, Keurig w/coffee. Swing set & trampoline for kids. Private outdoor set up w/(year-round) hot tub, dining area, fresh water sink & fire pit await you. Wonderful bakery & outdoor store 10min away. Enjoy Gunks glamping with a relaxing spa!

5 Acre Modern A-Frame with Barn and Game Room

A stone’s throw from the Hudson valley wine trail and state parks, this modern A-frame sits on a 5 acre former horse farm, providing privacy without isolation. Only 2 hrs from NYC, it’s perfect for weekend trips or longer getaways. Start the day with coffee on the wraparound deck, work remotely with pastoral views, then head out hiking or enjoy the game room. Evenings can be spent roasting marshmallows under the stars and unwinding in the clawfoot tub. As of Sept '25 - now with upgraded wifi!

Cozy & Spacious Country Home - All Seasons

We welcome you to stay at our inviting home in the hamlet of High Falls. The two-story early 1900's era farmhouse is set on 12 private acres off a quiet country road in a lovely residential area. Grounds feature access to woods & pond + the canoe-ready Roundout Creek. A large sunlit family room, a variety of games, vast outdoor space with patio furniture, in-ground pool/deck/BBQ/swings/firepit/hammock offer the perfect place to relax and restore your connection to nature, friends and family.

The Laurel Cabin

Tucked away in the serene Catskill mountains, this charming cabin has undergone a recent top-to-bottom renovation. Located just a short 5-min stroll from the vast expanse of the 30,000-acre Sundown Wild Forest, you'll discover endless trails, picturesque waterfalls, and abundant wildlife to explore. Additionally, within a mere 20-minute drive lies the stunning Minnewaska and Mohonk. We warmly welcome up to two well-behaved, non-aggressive dogs, although we regretfully cannot accommodate cats

Cozy Cottage | Sauna + Stone Patio w/ Firepit

Escape to a serene cottage nestled on the Shawangunk Ridge. Unwind by the fireplace, soak in the private infrared sauna (with direct patio access), or relax outside on the natural stone terrace with a firepit and forest views. Crafted with care—from a 100-year-old reclaimed wood dining table to a curated “meaningful library” and hidden messages—this space invites calm, curiosity, and connection. Near trails, lakes, and local adventure. Thoughtful, cozy, and quietly unforgettable.

Historic 1750s Farmhouse Apartment

Come explore the Hudson Valley from our newly renovated modern farmhouse apartment in a serene, bucolic setting. Located at the boundary of the towns of Gardiner and Shawangunk, beneath the beautiful Shawangunk ridge, there are plenty of adventures to be had! Hiking, biking, climbing, yoga class, and even sky diving are right here! And when you tire of all the outdoor fun, check out local wine, cider, and whiskey tastings, antiques shopping, and delicious local restaurants.

Tiny cottage on DiR mini farm

A custom made tiny cottage, located on a private tree lined road with just a few houses on it. The design style is farmhouse rustic with original details. It is private, fully equipped, and centrally located. The front of the cottage has a sun drenched porch equipped with lounge chairs and bbq. The back of the cottage is has a screened in porch, an outdoor huge tub and lounge. It is facing a beautiful pond, a fire pit and deep woods and vibrant nature.

Stone House 1807. Comfort, Peace and Nature.

Historic 200 yr old stone cottage, on three floors, renovated to a high standard, creating a very comfortable and peaceful retreat, whilst retaining soul and character. Extreme cleanliness is a priority. Quality bedding assures a good nights sleep. The bathroom offers a rain shower and soaking tub. The kitchen is fully equipped and fresh produce is available from the neighboring organic farm in season. Good hiking trails are accessible from the house.

Leggett Cottage

Located in historic High Falls on Leggett Road, one of the loveliest roads in the area, is your private cottage. Just renovated, it has all new amenities. The location is steps away from the rail trail where you can bike or walk. Stone Ridge and High Falls are a half-mile away for all your shopping. Situated between the majestic Shawangunks and the Catskills; outdoor activities, farm to table restaurants, breweries and farmers markets abound.

The Cabin at Pleasant Valley Farm

The cabin is located on a dirt road on our farm with a beautiful pond and an amazing view! This off-grid, cabin has two queen beds (100% cotton sheets), a mini-kitchen with a battery-ignition gas range, solar powered refrigerator, solar lighting, a wood stove, an outdoor shower, a fire pit, and an old-fashioned outhouse. An expansive porch and dock provide comfortable outdoor living. A seasonal favorite, the cabin is available May-Oct.