Family-friendly vacation rentals in Cragsmoor

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Top-rated family-friendly rentals in Cragsmoor

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Top guest favorite

A wide view of a grassy field is presented, bordered by trees and rolling hills in the distance. The sky appears clear and blue, creating a serene backdrop for outdoor activities. A small firepit made of stone is positioned on the lower left.

Campsite in Kerhonkson

4.94 out of 5 average rating, 139 reviews

tent camping $25/person/night -stunning mt views.

Hi- this is private tent camping on a horse farm in kerhonkson, NY It is not a campground! $25/ person per night! Many sites so even if it shows booked , reach out to me!! There is no water or electricity but you can have a small fire if conditions allow. Yes, portajohn. You can drive your car to the site which is in a field. Check in /out noon Quiet, respectful and law abiding folks only! We know people need some fresh air, leg stretching, stars,connecting to nature & change of scenery.

Guest favorite

The interior of the bus features a cozy layout with a full bed and a twin bed, both with new linens. A rustic storage unit is present along one side, while soft overhead lighting and a small dining table enhance the warm ambiance. A compact electric fireplace adds comfort.

Bus in Pine Bush

4.93 out of 5 average rating, 178 reviews

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/AC, mini-fridge, Keurig w/coffee & mugs. 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 just down the road. Enjoy Gunks glamping with a relaxing spa!

Guest favorite

Cottage in Ellenville

4.95 out of 5 average rating, 160 reviews

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

Top guest favorite

A modern living area is showcased, featuring a plush dark sofa and a live-edge coffee table at its center. Large sliding glass doors provide expansive views of the surrounding landscape, while polished concrete floors complement the wood-paneled ceiling. A flat-screen TV is mounted for entertainment.

Chalet in Cragsmoor

5 out of 5 average rating, 247 reviews

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.

Top guest favorite

A dining area features a round table covered with a patterned tablecloth, surrounded by wooden chairs. Bright yellow walls and large windows allow natural light to fill the space, complementing the vintage wooden sideboard adorned with decorative items.

Home in Cragsmoor

4.89 out of 5 average rating, 135 reviews

Mountain Top Escape with Hot Tub - Blue Heaven

Connect with friends and family while sipping coffee on the porch and watching for deer, wild turkeys or humming birds. Share some of the fruits of our garden and cook in the fully equipped kitchen or grill on the porch after hiking, touring or just hanging out in hammock. Play air hockey in the attic or games or do a puzzle. Later, warm up by the wood stove, with a glass of wine or a book, get the chill out in the hot tub and see the stars or roast s'mores in the fire pit.

Guest favorite

A tiny house adorned with colorful outdoor lights stands against a night sky. Trees frame the property, while a bright moon casts a soft glow, adding to the serene atmosphere of the setting.

Tiny home in New Paltz

4.99 out of 5 average rating, 847 reviews

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. Enjoy wildlife or relaxing at the river bend on our 5-acre property or explore the awesome attractions close by: county pool, winery, New Paltz downtown, “gunks” rock climbing, Minnewaska State Park, and more!

Top guest favorite

Cottage in Kerhonkson

4.82 out of 5 average rating, 927 reviews

Cozy Cottage w/ Infrared Sauna

Escape to a serene, nature-inspired cottage nestled on the Shawangunk Ridge. Relax by the warm gas fireplace, gather around the handmade dining table crafted from 100-year-old reclaimed wood, or unwind in the private infrared sauna, accessible from the master bedroom. Explore nearby hiking trails, discover hidden messages throughout the space, and enjoy a curated "meaningful library." Perfect for relaxation, adventure, and meaningful moments with loved ones.

Top guest favorite

A peaceful landscape featuring a spacious yurt set amidst a grassy field, with the stunning Millbrook Mountain cliffs visible in the background. The clear blue sky complements the scene, accentuating the connection to nature and the serene surroundings.

Yurt in Gardiner

5 out of 5 average rating, 286 reviews

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.

Guest favorite

The farmhouse, showcasing classic white siding, is framed by lush greenery under a soft, cloudy sky. A wooden deck extends from the side, enhancing the inviting exterior. The structure features two stories, with a chimney and well-maintained landscaping surrounding the property.

Home in Kerhonkson

4.97 out of 5 average rating, 153 reviews

Farmhouse Fantasy!

Welcome to your Farmhouse Fantasy! Come enjoy a weekend in the country, just two hours from NYC. Built in 1900, the home was recently gut renovated and features two spacious bedrooms, full bathroom, open plan dining room and living space, a three-season sun room, back deck, and a modern and well appointed kitchen. Located just minutes from Minnewaska State Park and all the beauty and fun the Shawangunks have to offer!

Top guest favorite

A red wooden cottage is surrounded by lush greenery, featuring green window shutters and a covered porch. A wooden rocking chair is visible on the porch, inviting relaxation. The upper level includes a balcony that overlooks the picturesque landscape.

Cottage in Pine Bush

5 out of 5 average rating, 118 reviews

Catskills Cottage (w/ Hot Tub) on Top of the World

Escape the city for a romantic winter getaway or a weekend with family/friends at this historic 3 bdrm mountaintop cottage in the famed artists colony of Cragsmoor. The house sits atop a dramatic cliff and has decks on both floors--including a new cedar hot tub!--with stunning views of 50+ miles of the Catskills Mountains, Minnewaska State Park and the Shawangunk Ridge. Less than 1.5 hours from NYC.

Guest favorite

The exterior of a historic stone farmhouse is shown, featuring a vine-covered wall and landscaped garden. Steps lead to the entrance, surrounded by greenery and floral elements, with large windows allowing natural light. The serene outdoor setting reflects the charm of the surrounding countryside.

Apartment in High Falls

4.78 out of 5 average rating, 624 reviews

Art Room at Old Stone Farmhouse

Downstairs Victorian style private suite with it's own entrance to large front hall, bedroom & bathroom in an old stone farmhouse filled with mid-20th-century artwork. Easy access to outdoors. The house is one of the original deeds in Clove Valley dating back to the 1700s. The home has lots of character on a sustainable farm adjacent to the Mohonk Preserve & 7 miles to Minnewaska State Park.

Guest favorite

Cabin in Ellenville

4.99 out of 5 average rating, 153 reviews

Catskills Cabin, Hot Tub, Wood Stove, King Bed

Welcome to Minnewaska Cabin. A Catskills mountain cabin on a private forested lot, with a hot tub, a wood stove and king bed. The house is brand new (completed Dec 2023) and located about 2 hours from NYC, close to many local attractions 20 mins from Minnewaska State park 35 mins from Legoland Goshen 20 mins from Resorts World Catskills casino 5 Mins from North East Off Road Adventures