Family-friendly vacation rentals in Round Top

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Round Top

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Guest favourite

Home in Windham

4.88 out of 5 average rating, 134 reviews

Live the Slow Life at an All-Season Mountain Escape

A private, spacious 4 bedroom house located in the Catskills Mountain, in the Town of Windham, NY just 2 hours from New York City. Perfectly suited for all 4 seasons. Minutes away from Windham Mountain Resort, the Northeast’s year-round outdoor lifestyle destination and about 20 minutes to Hunter Mountains. Wake up to breathtaking views of the mountains all year-round from large windows. Four bedrooms: 2 with queen size beds; 1 with bunk bed (twin and full size bed at the bottom) and 1 with two single beds. Five Star Cottage comfortably sleeps 8 to 9 guests. The main floor has a open floor plan, multiple large skylights and views of Windham Mountains. Cozy living room with wood burning fireplace, Smart TV with WiFi plus dining area with table that seats 6 and opens up to accommodate 10. Full kitchen with upgraded stainless steel appliances. A bedroom with 2 single beds. Also, a half bath and spa room are located in the main floor. Large deck with seating and gas grill to enjoy life outdoors. The top floor have 2 bedrooms (one with a private balcony), a full bath with tub and shower. Catwalk overlooking the living room on the main floor. The lower level is home to one bedroom with a queen size bed, a full bathroom with shower and tub plus a beautiful den with a large sectional sofa, Smart TV with WiFi and multiple board games. Plus, laundry room with new washer and dryer. Walk out into the yard from lower level and enjoy life outdoors. Guests will have full access at Five Star Cottage which includes 4 bedrooms, 2.5 bathrooms, full kitchen with pots, pans and utensils, family room, two TV's with WiFi, den, laundry room with washer and dryer, spa room with hot tub, private balcony, large deck and 2-acres of land. Please contact me for instructions to get access to the house. The cottage is within minutes of Windham Mountain, the closest ski resort to NYC. Hiking trails and golf courses are nearby, as are places to go mountain biking and horseback riding. Nearby Windham Path is a family-friendly spot for novice hikers. The best way to get around is by car.

Guest favourite

Guesthouse in Woodstock

5 out of 5 average rating, 362 reviews

Steps toTown/Bus Pet Ok/No Extra Fees! &Five Star

PRIVATE Modern/Rustic Apt WALK TO ALL 5 * Rating "premiere" NO EXTRA CHARGES! 1000 sq ft Pet Friendly n/c Park Master King Suite &I can put up 2cots /crib Full Kitchen Cathedral Living Room w/Mountainview. 1&1/2 Bath Deck for Outside Dining w/Mountainview WOOD FIREPLACE on deck Wi-Fi Wash/Dryer Gas BBQ Steps to CTR of Town Green & NYC Bus-stop, THE COLONY, Yum Yum, Goodnight , Garden Cafe, Silvias, Bread Alone, Mud Club, Station Bar, shops . Cemetery's Bubbling Stream, PrivatePlayground

Guest favourite

Apartment in Halcott Center

4.97 out of 5 average rating, 139 reviews

Mountain View Apartment

We offer a quiet and extremely clean place. We are only 6 miles from Belleayre Mtn Ski Center. Restaurants are nearby. You’ll love our place because of the neighborhood, the outdoors space, the light, and the kitchen. Our place is good for couples, solo adventurers, and business travelers. WIFI is 300mbps. We have security cameras outside only, EV Charging station on the property. We now have an outdoor fire pit (wood not included). We also have a standby generator in case of a power failure.

Guest favourite

Home in Round Top

4.96 out of 5 average rating, 191 reviews

Escape in the Catskills w/hottub

Escape to the Catskills: Your Mountain Retreat No Cleaning Fee! Immerse yourself in the breathtaking beauty of the Catskills. Our cozy retreat offers the perfect blend of relaxation and adventure, whether you're seeking a romantic getaway, a peaceful remote work haven, or an exciting outdoor adventure. Unwind in the hot tub while enjoying stunning world-class panoramic views. Conveniently located near charming towns with unique shops, delectable dining options, and hidden antique treasures.

Guest favourite

Home in Lake Katrine

4.95 out of 5 average rating, 111 reviews

Waterfront 3BR Home in Hudson Valley, Catskills

Key Residence Features at a glance; Waterfront on the Esopus Creek, Seasonal Kayaks, Rowboat, Dock (approx. Memorial Day weekend-mid October) large yard. Fully equipped kitchen, cable, wireless internet, washer and dryer. Enclosed porch, deck and patio with propane grill and patio furniture. Paved flat driveway, ramp allowing access to first floor, oversize door to first floor bathroom. Three spacious bedrooms with air conditioners. Convenient location close to thruway exits. No boat launch.

Guest favourite

Home in Saugerties

5 out of 5 average rating, 147 reviews

Upstate Modern Scandinavian Barn in the Catskills

Renovated 1850's barn with 3 bedrooms and an ample loft space that can serve as a fourth. The house also has a large rec room with cathedral ceiling buttressed by hand-hewn beams, well-equipped kitchen, Scandinavian wood stove, sauna, home gym, and projector. Outside: 2 private decks with amazing views of Overlook Mountain, private grill, private hot tub. On property: shared tennis court, swing set, fishing pond, heated pool (summer only). 2 hours from NYC, 10 min. to Woodstock & Saugerties.

Guest favourite

Home in Athens

4.84 out of 5 average rating, 170 reviews

A Victorian "Lady"

Enjoy an old-fashioned vacation right across the street from the Hudson river. Watch the tides, boats, and barges pass by. Dining, kayaking within walking. Historic Hudson, Olana just 10 min. drive. This is a house to relax, use as a base for other activities. It is not intended as a place to party.. It is a quiet neighborhood. I expect my guests to respect that. There is a weekend special. If you book friday/saturday or saturday/sunday the price is $350.00 for the 2 nights. Thanks

Guest favourite

Home in Woodstock

4.98 out of 5 average rating, 216 reviews

Sweeping mountain views in Woodstock, NY

A quick 3 minute drive to the center of town, our recently built 3 bedroom house has gorgeous mountain views and is on 5 beautiful secluded acres surrounded by trees. The property is fantastic in all seasons and close to amazing Catskill skiing, hikes, waterfalls, swimming holes, and the Hudson River, as well as the towns of Phoenicia, Saugerties, Kingston, Catskill, Hudson, Rhinebeck, and Tivoli. In winter we have the best sledding hill in town! Follow us on Insta @ohayowoodstock

Guest favourite

Home in Kerhonkson

4.95 out of 5 average rating, 351 reviews

Ask About Winter/Spring Discounts!

Look from the luxurious spa tub at the countryside oasis atop a rolling knoll on the edge of fir-scented forest land. Come home from a hike, farm, or award winning restaurant, & snuggle up by the fire under grand cathedral ceilings. In summer, swim in the salt water pool & enjoy the fire pit surrounded by lush landscaping & quiet. Stunning views as the seasons change, the windows showcasing rolling snowy hills or the vibrant colors of autumn leaves climbing the mountains.

Guest favourite

Apartment in Shandaken

4.8 out of 5 average rating, 188 reviews

Catskill Cabin, Chill Apartment, 1st Fl * * * * *

Natural fineness meets charming style. Follow us @alpinefourseasonlodge for connections, recommendations and the enjoy-full life. We focus on healthy living, the environment & sustainability. Every day something in nature, a bear in the bushes, picturesque autumn foliage perfect for hipsters and dudes, kids and us grownups. Enjoy the mountain views. The Farmhouse is surrounded by miles of preserved forest land. Enjoy the mountain views. Parties or events are not allowed.

Guest favourite

Home in Palenville

4.95 out of 5 average rating, 151 reviews

Serenity Retreat: Mountains, Waterfalls, Comfort

Enjoy a tranquil retreat overlooking a peaceful creek, set against gorgeous mountain views and nearby spectacular waterfalls. Just a short drive from Woodstock and Saugerties, NY this home on a serene country lane is a gateway to nature's beauty. With close proximity to local attractions, a lush garden, stunning mountain vistas, and a family-and-pet-friendly yard featuring a fire pit and bad mitten, it's the perfect blend of comfort and adventure.

Guest favourite

Home in Denver

4.98 out of 5 average rating, 139 reviews

Hilltop Hideaway - best Catskills views!

Best view in the valley! Come relax on the patio, breathe in the fresh mountain air and watch the clouds pass through the vista below. The house is located on a private road for ultimate serenity, convenient to the charming town of Roxbury. 3 bedrooms, a full-height sleeping loft, 2 full baths and fully appointed kitchen make this a perfect destination to relax with family and/or friends. Pets allowed with approval. 4WD/AWD car essential in winter.