Family-friendly holiday rentals in Cragsmoor

Spacious A-Frame Getaway near Hiking and Wineries

Escape to our A-frame in the heart of the Shawangunks, nestled within the picturesque Hudson Valley. Just 1.5-2 hours from NYC, our spacious and serene home is perfect for a peaceful retreat, outdoor adventures, and exploring local wineries. Nearby attractions include Lake Minnewaska Park, Mohonk Preserve, Sam’s Point, the Shawangunk Wine Trail, Ellenville and Blue Cliff Monastery. The location also provides convenient access to explore many of the Hudson Valley and Catskill towns and villages.

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!

Romantic Apartment in Historic Stone Ridge

Relax in this cozy apartment in our beautiful colonial house in the middle of historical Stone Ridge, NY. It offers perfect mixture of rustic and modern styles and is decorated with original art. Full kitchen is equipped with everything you need to prepare a great meal. It is perfect for all seasons and located within walking distance to restaurants, coffee shops, yoga studios, groceries. New Paltz, Woodstock, Minnewaska, Mohonk Preserves, Shawangunk Ridge are all within the short 20 min drive.

Shingle Gully Cottage

The Shingle Gully Cottage is located on over 40 acres of privately-owned land bordering Sam’s Point Preserve. The cottage is located on the outskirts of Ellenville NY. The town is situated at the base of the rolling Catskills within the Shawangunk valley. Within the cottage, there is a pellet stove that will be lit on chilly nights upon request. During the summer months, there is air conditioning available making a cool and cozy retreat from the heat of the summer. Ask about Minnewaska/Sams Pt

Scandinavian-Style Chalet with Scenic Views

Wake up to hilly views from this Scandinavian-inspired chalet boasting wood-paneled cathedral ceilings, sharp furnishings, and concrete floors. Share a glass of wine with a friend beside a sleek fireplace and live-edge coffee table in a chic living area. Please inform the host if you plan to bring a dog as there is a 15 pound weight limit. Maximum number of guests/visitors/people permitted on the property is 2. The owner lives on the property and is available for anything guests may require.

Sweet Cottage on a Farm Road

Simple, airy, studio cottage next to my house, featuring a woodstove & enormous bathroom with a clawfoot tub. Perfect for writers/solo-travelers seeking solitude & peace and couples wanting quality time together. The cottage is on a scenic country road, walking distance to 3 farms, including 2 great farm-to-table restaurants: Westwind Pizza/Apple Orchard, Arrowood Brewery, & Hollengold Farm. A stone's throw are Stonehill Barn and Inness. 15 min drive to the incomparable Minnewaska State Park.

Stylish and Cozy Mountain Retreat

Private entrance into a stylish, cozy upstairs studio in artist's mid-century home near The Ashokan Reservoir. The Catskills are the destination for hiking, art, skiing, swimming or checking out the local food scene and breweries - all within minutes. Guests have the second floor to the home with no shared spaces with host. Outdoor seating with grill, barn with bocci and other yard games. King size bed, day bed with plush bedding. Spacious new bathroom with tiled shower and skylight.

Cozy Catskills Cottage

Welcome to our cottage! We have 4.5 acres in the Catskills which includes a cozy cottage overlooking a babbling brook and next to a adorable duck pond. Come for peace, privacy, and relaxation that's only 2 hours from NYC. Cottage, 1 Bedroom, two floors, 800 sq. ft., full bath, fully furnished with a deck and patio furniture. Set back in the woods on a shared property off a beautiful farm road in Kerhonkson. 10 minutes away from the Shawangunk mountains and amazing options for hikes.

Modern BoHo 3BR Cottage Near by Hiking, Winery

Our newly modern bohemian cottage (aka Green House!) is perfect for your next weekend getaway or a new WFH locale. Decompress from city stress in this calm, serenely appointed private home. Close to attractions but far enough away to escape, you'll never want to leave. NYC: 79 mi. Hunter Mountain Ski Resort: 60 mi. Pine Bush - groceries/supplies: 7 mi. Middletown - shopping (Walmart, Target, Best Buy, Home Depot): 16 mi. Hiking trails: 7 mi. Horseback riding: 7 mi. Sky diving: 15 mi.

Winter Sale - Cozy Cabin + hiking + pets welcome

Take a leisurely walk under the towering trees in the quiet wooded acre surrounding our cozy, alpine-inspired cabin with contemporary bohemian touches. Sleep in upstairs under deep-set skylights, observe wildlife out our large picture windows, or curl up by the fire on the rustic screened porch. Daydream on our hammock or dine alfresco taking advantage of our barbeque. On a clear night, it is easy to stargaze up through the tall trees, perhaps while toasting marshmallows fireside.

Hidden cabin on 2 wooded acres

Retreat to a beautiful cabin and get lost on two wooded acres. Reconnect with nature in your own way - hike around nearby Lake Minnewaska, or another of the dozens of incredible trails in the area. Explore infinity under a blanket of stars and share stories gathered around the firepit. When you’re called inside, grab a book and settle in by the fireplace. Then cook a meal in our well-equipped kitchen or on the grill, and enjoy it on the patio overlooking the property.