Family-friendly vacation 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.

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!

The Upstate Creek House

Built in late 1700, this modern Farmhouse on a creek is peaceful. You will see the original bones of the house through some of the lower ceilings & doorways on the 1st floor which gives this gem uniqueness. Lots of beautiful natural light. 200+ sq.ft screen enclosed porch, wood stove, outdoor fire pit, updated kitchen, 3 bdr & 2 bth, games-a-plenty, books-a plenty, & over 2,200+ sq.ft to enjoy. Positioned 90 minutes away from NYC, the house is central to everything you want to do in Upstate NY.

Modern 3BR BoHo Retreat/Nearby Hiking, Wineries

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.

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.

Fern - Kos Retreats @ Frogs Hollow Farm

Fern is one of the two luxurious yurts we offer on our 100 acre organic farm. It is gorgeous, bringing you as close to nature as possible without giving up any of the luxuries in life! 450 sq ft of living in the round, it includes a full ensuite bathroom (in the yurt), and your own private deck, firepit, and barbecue outside. We are 15 minutes away from New Paltz, NY, and mere minutes away from the Shawngunk Mountains in the bucolic Hudson Valley.

Luxe modern A Frame, Hot tub and new heated pool

Experience the luxury of this black double A-frame, finished to the highest standards and nestled in the woods for ultimate privacy. The main bedroom features a soaring ceiling and spa-like en-suite with walk-in shower, tub, bidet, double sink, and heated floors. The sunny second bedroom also has an en-suite. Enjoy a chef’s kitchen, double-sided fireplace, hot tub, and a new pool available June. Pets must be disclosed and approved prior to booking.

Modern Zen Chalet at the Foot of Gunks w Mt. View

Kick back at the foot of the Shawangunk Mountains in this calm, stylish home. Surrounded by forest, the house features large picture windows in every room to help you reconnect with nature. Enjoy the natural stone porch with a fire pit and newly built barrel sauna. Located near Minnewaska State Park, with quick access to trails, and views of Millbrook Ridge and the Gunks’ iconic climbing routes right from the windows.

Black A-Frame: Catskills Cabin

Escape to Black Pines A-Frame, a fully renovated 1961 cabin nestled in the Catskill Mountains in Kerhonkson, NY. Named one of the “Coolest A-Frames in NY” by the New York Post, this charming retreat blends rustic character with modern comforts. Set on two private acres, it offers stunning wooded views and a warm, inviting atmosphere.