Family-friendly vacation rentals in Maryland

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Maryland

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

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Guest favorite

Home in Windham

4.88 out of 5 average rating, 135 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 favorite

Home in Canajoharie

4.92 out of 5 average rating, 157 reviews

2 homes on large private mountain views getaway

Rent these 5 bedroom 4 bath houses for your next vacation. House sits on top of a hill and has breath taking views, amazing sunrises from the master suite and sunsets from the great room. Home has octagon shape great room with open timber ceiling, large indoor fireplace. Very large and great kitchen for your cooking. Studio has a projector style TV 100 plus inches. Red House/game room with additional 3 queen log beds, full kitchen and bathroom, laundry etc. This home has beautiful open timber.

Guest favorite

Apartment in Halcott Center

4.97 out of 5 average rating, 140 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 favorite

Cottage in Roxbury

4.9 out of 5 average rating, 130 reviews

Bellwood Cottage 8-14min to all Roxbury Wed Venues

Bellwood Cottage is perfect for couples, families, or groups of friends looking to get away from it all in an private, idyllic setting. Great for all seasons and close to skiing (20-40 min from Plattekill, Belleayre, Hunter and Windham), hiking, fishing, swimming holes, restaurants and quaint towns. Walk to downtown Roxbury and Kirkside Park via the scenic rail trail. Close to all wedding venues - 4 miles to Roxbury Barn, 7 miles to Stone Tavern Farm, 4 miles to The Inn at West Settlement.

Guest favorite

Home in Lanesville

4.95 out of 5 average rating, 157 reviews

Waterfront, outdoor deck with fire pit

Enjoy the fresh mountain air and relaxing vibe hosted by Mother Nature herself. Located on Main St. in Hunter - 3 min walk from the bus stop, 8 min walk to Hunter Mt if you choose (2 min drive w. Car/ski equipment) Cozy and comfortable house that overlooks Hunter Mountain. Private waterfront access to the Schoharie creek, good sized sunken backyard w fire, upper and lower patios - Sleeps 6 in beds, 2 more on the sofa bed. 2 full baths, washer and dryer, wifi and Smart Tv's with built in Roku

Guest favorite

Cabin in Prattsville

4.83 out of 5 average rating, 168 reviews

Modern Cabin CLOSE TO SKI w/HOT TUB, VIEWS & Games

Welcoming you to the beautiful Catskills with our renovated (May 22') Modern Cabin with a Private SWIM POND situated on 6 acres w/ lovely and expansive mountain views and backed to 240 acres of NYC DEP LAND FOR HIKING, HUNTING & MORE!! The House is fully stocked to be enjoyed for all seasons! Take a dip, boat, fish or ice skate on the POND. Relax in the HOT TUB or lounge in the HAMMOCK or ADIRONDACK Chairs around the FIRE PIT while enjoying the views!! Enjoy grilling on the GAS GRILL!!

Guest favorite

Home in South Kortright

4.99 out of 5 average rating, 108 reviews

⭐A Secluded Schoolhouse Stay⭐

South Kortright Schoolhouse No. 5. A recently renovated, authentic former one-room schoolhouse located in the northern Catskill Mountains.This cozy space offers couples a romantic getaway and families a place to connect with the surrounding farmland. Schoolhouse No. 5 neighbors a working sheep farm with many fun activities available for guests. Visit the draft horses, chickens and turkeys, or help with daily chores. Bring your dog along for the journey, but please keep them leashed.

Guest favorite

Apartment in Shandaken

4.81 out of 5 average rating, 190 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 favorite

Home in Oneonta

4.89 out of 5 average rating, 160 reviews

1st Class Rentals Munson Manor III at Murdock

**** Summer rental from June to August please use ONE guest for the pricing. Also check out time is 9 am *****From September to May please list the number of guests staying to get the proper pricing. We charge additional fees after 2 guests. Check out time is 11 am. *****We also have a $100 fee for a pet (dogs only) per stay. Location is awesome! This 5 bedroom, 2 bathroom home is located on a quiet street with several restaurants within walking distance.

Guest favorite

Home in Denver

4.98 out of 5 average rating, 140 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.

Guest favorite

Cottage in Livingston Manor

4.99 out of 5 average rating, 153 reviews

Nicks Place

Open space kitchen, dining, and living room All in a cozy country setting . Two bedrooms with queen beds and two single beds in spacious loft. Bright and sunny. Outdoor grille, firepit, and sun porch. Close to hiking trails, one mile from state gamelands. Minutes from Beaverkill and Willowemoc rivers. Close to three local breweries and distillery. Within an hour of ski resorts. Super quiet location, off the beaten path.

Guest favorite

Cabin in Jefferson

5 out of 5 average rating, 477 reviews

"Far from the Madding Crowd" Cozy Cabin Retreat

Cabin Clack is a quiet, stream-side retreat bordering 1000 acres of wild trails in NY State Forest. The cabin is a historic hunting cabin from circa 1935. The cabin is good for a couple, solo adventurers, or families (with kids). We welcome pets, and they will love exploring the secluded forest and the freedom of our virtually traffic-free dead-end road. There is a spring fed pond you can swim in.