Family-friendly holiday rentals in Cragsmoor

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Cragsmoor

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

1 of 1 pages1 / 1

Top Guest favourite

A spacious living area features large glass doors that bring in natural light and provide views of the outdoors. Comfortable seating includes a modern sofa and armchair, accompanied by a coffee table and a dining area positioned nearby.

Chalet in Pine Bush

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.

FamilyIndoor spacesHiking

4.97 out of 5 average rating, 142 reviews

Top Guest favourite

A contemporary house is displayed, featuring a sleek exterior of wood and metal. Expansive windows offer a view of the surrounding trees. A spacious deck extends from the structure, providing a seamless transition to the outdoor environment.

Home in Accord

Accord River House

Welcome to our house in the woods! 12 acres surrounded by trees and above a series of waterfalls along the Stony Kill, which runs all the way from Minnewaska State Park through our property and into downtown Accord. You can sit in a hammock outside, soak in our hot tub while listening to the river, or chill out inside with some tunes or the TV projector. Budding entomologists will enjoy the endless procession of bugs, ants, spiders, ticks, and other creepy-crawlies that is part of River House.

KitchenIndoor spacesCondition

4.99 out of 5 average rating, 106 reviews

Superhost

An indoor heated swimming pool is featured, surrounded by wooden paneling and illuminated by colorful LED lights. A hot tub is positioned beside the pool, with two lounge chairs placed nearby. Large windows offer views of the exterior while maintaining a cozy atmosphere.

Home in Newburgh

Entire Home, Private Indoor Pool

This unique specious and tranquil getaway private home includes an indoor heated swimming pool, hot tub, an outdoor space of 34 acres for you to enjoy nature, work out equipment, movie theater. Complete eat in kitchen, outdoor grill. washer and dryer, three bathrooms. Huge open space basement equipped with LED changing color light. Rooms have Wi-Fi LED light to connect music. The place sleeps 8 guests, in beds. Two additional twin mattresses.16 guests maximum. Hot tub take a while to heat up.

Indoor spacesFamilyHeating

4.81 out of 5 average rating, 136 reviews

Top Guest favourite

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

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.

KitchenIndoor spacesTV

5.0 out of 5 average rating, 255 reviews

Top Guest favourite

A castle-style retreat is showcased, featuring a whimsical dragon statue and a large chess set in the foreground. A tranquil pond with a fountain is visible, alongside a magnificent castle structure designed with classic stone elements and a welcoming entrance, all set amidst lush greenery.

Castle in East Stroudsburg

Pocono Castle: Dungeon Escape Room & Private Pond

Sleep in a Fairy Tale at Pocono Castle! Live the dream in this 2,300 sq. ft storybook retreat, where you’ll sleep like royalty in a real fairy tale castle. Unwind in luxury with a bubbling hot tub, a cedar sauna, and endless magical touches. Dress up as Kings, Queens, or Knights and explore the grounds, featuring a private one-acre pond & maybe you’ll catch a Golden Fish! With enchanting bedrooms, outdoor adventures, and unforgettable charm, this is the OMG getaway you’ve been waiting for!

Indoor spacesKitchenHot tub

4.99 out of 5 average rating, 475 reviews

Top Guest favourite

A spacious log cabin features a welcoming wraparound porch with wooden railings. The two-story structure boasts a combination of gabled roofs and large front windows, surrounded by lush green landscaping. A paved driveway leads up to the entrance, enhancing the environment's rustic charm.

Cabin in Pine Bush

NEW! Foley's Riverfront w/ Hot Tub-LEGO LAND CLOSE

Escape to the ultimate Hudson Valley retreat when you stay at this 4-bedroom, 3-bathroom vacation rental Log Cabin in Pine Bush! The property is situated on 6 private acres of land and boasts an extensive 3,500 square feet of rustic paradise, making it ideal for large families or groups of up to 12. Enjoy amenities such as a hot tub, game room, and home theater, which are sure to elevate your experience. Explore the numerous outdoor activities nearby as. well as the NEW LEGO LAND NEARBY!

FamilyKitchenAccuracy

4.89 out of 5 average rating, 233 reviews

Guest favourite

A modern dining area features a wooden table surrounded by stylish chairs. Five pendant lights hang above the table, providing soft illumination. A plant stands nearby, contributing to the fresh ambiance, while a sliding door offers access to outdoor space.

Cottage in Pine Bush

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.

FamilyKitchenComfort

4.93 out of 5 average rating, 133 reviews

Guest favourite

Cottage in Napanoch

Mid century house on 100+ acres…

Discover serenity in our newly renovated mid-century ranch house nestled on 100+ acres of forever wild land, where modern comfort meets 1950s charm. Whether savoring wine, engaging in board games, or relishing classic vinyl records, every moment is enveloped in tranquility. Wake up to breathtaking views of the Shawangunk and surrounding forest from the expansive back deck. Perfect for morning coffee. Get lost exploring the secluded beauty that surrounds this picturesque retreat.

FamilyKitchenLaundry

4.82 out of 5 average rating, 103 reviews

Top Guest favourite

A spacious wooden deck is displayed with a large table at the center, surrounded by several white chairs. Two lounge chairs are positioned to one side, offering views of the surrounding greenery and trees. The deck's railing features a wire design, enhancing the open feel.

Home in Kerhonkson

Spacious and quiet - a dream Catskills getaway

Welcome! Just two hours from Manhattan, our home is the perfect Catskills getaway. Tucked into the woods at the base of Minnewaska state park, our home is quiet, clean and full of light. The house is surrounded by green and nature, but close to cute towns for shopping and dining and of course all the area has to offer with hikes and outdoor activities. Or stay in and lounge on the deck, listen to some records, watch a movie, and relax. It's everything you need for a dream vacation.

Indoor spacesKitchenBackyard

4.97 out of 5 average rating, 169 reviews

Guest favourite

The cottage is set on a spacious lawn, surrounded by trees, showcasing a well-maintained exterior with a gray facade and a gravel walkway leading to the entrance. A chimney indicates the presence of a cozy fireplace inside.

Cottage in Ellenville

Shingle Gully Cottage

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, situated at the base of the rolling Catskills within the Shawangunk valley. 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. There are two additional cottages on the property.

Indoor spacesFamilyNearby

4.94 out of 5 average rating, 177 reviews

Superhost

Cabin in Ellenville

Dreamy A-Frame Cabin Hot-Tub | Games Room | Firept

Welcome to our 3 bedroom, 1.5 bathroom A-frame mountain escape with room to spread out and unwind. • Hot tub, fire pit, overhanging deck, and outdoor dining patio • Cinema-style movie room, pool table, darts, board games, and record player • Fully kitted gym with water rower, free weights, kettlebells, and more • Catskills foothills base, with short access to lakes, waterfalls and breathtaking hikes Book your stay and enjoy the cabin’s mix of play, rest, and forest views.

Indoor spacesFamilyWalkability

4.89 out of 5 average rating, 300 reviews

Guest favourite

The modern cabin is set within a forested area, featuring a sloped roof and large windows. A private patio is furnished with a seating area and a hot tub is positioned nearby, surrounded by stone. The natural landscape enhances the serene setting.

Cabin in Ellenville

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 very new (completed Dec 2023) and located about 2 hours from NYC, close to many local attractions, like hiking trails, skiing and water sports. 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

KitchenIndoor spacesAmenities

4.98 out of 5 average rating, 232 reviews