Family-friendly holiday 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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Top guest favourite
A rustic cabin is set against a backdrop of lush greenery, featuring a spacious wooden deck with a dining table and chairs. Inside, a cozy sleeping area showcases a neatly made bed with soft linens, while the warm wood interior adds to the inviting ambiance.
Cabin in Oneonta
4.99 out of 5 average rating, 178 reviews

Romantic Cozy Cabin with a View of the Wetlands

Summer baseball renters please note: availability is Dreams Park tournament schedule ONLY -- not All Star! Perfect for a couple's getaway, a writing retreat, or a cozy home base to explore the area! Built in the 18th century, it now boasts an adorable fully-equipped kitchen, a charming wood interior, a vaulted ceiling, and a spacious deck with a view of the birdlife and wetlands. Swimming, hiking, and fishing on Goodyear Lake 5 mins away! Minutes from live music, cafes, and antique shops!

Top guest favourite
A covered patio area features two turquoise chairs and a round table positioned on a wooden deck. A small refrigerator and microwave are visible in the background. A decorative rug adds texture to the space, while a nearby hammock invites relaxation.
Guest house in East Meredith
4.97 out of 5 average rating, 156 reviews

The Lily Pad

If you want to experience nature, our homestead has a separate one room king bed cottage, with a front porch, between 2 ponds. A private full bath is 25 steps away (attached to our home for plumbing purposes). Enjoy the serenity of the ponds and birds. The cottage is insulated, heated, has electricity,Wi-Fi, and a smart tv to be used with your own accounts. Fishing pole provided. The cottage is separated from our home by a garage. We leave guests uninterrupted unless they want/need anything.

Top guest favourite
A shaded outdoor dining area is surrounded by lush greenery, featuring a circular table with wrought iron chairs on a stone patio. In the background, a charming red house is visible, framed by trees and the distant mountains.
Home in Davenport
4.96 out of 5 average rating, 120 reviews

Cooperstown Vicinity Country Home near Motorsports

Charming open concept house nestled in the Catskill mountains 20 min E. of Oneonta. Exquisite Views! (**Adjacent to motorcycle racetrack. It's not visible, but noisy in daytime 9am-5pm 4-5 days/wk.) Enjoy a morning read in our comfy sofas and armchairs or get cozy by the gas fireplace at night. Explore our 20-acre property or relax out on the wide, sunny lawn. Outdoor table and chairs by the firepit are perfect for an evening meal overlooking the beautiful, ancient Catskill Mountains.

Top guest favourite
Cabin in Walton
4.94 out of 5 average rating, 196 reviews

The Mill House: An Enchanting Stream-Side Retreat

Nestled in the heart of the Catskills and just a 2.5-hour drive from NYC, escape to the perfect fall retreat where you can reconnect with nature and enjoy the serene beauty of the season. This historic gem underwent a recent restoration, marrying its saw mill heritage with contemporary luxuries, including a Nest thermostat, smart speakers, keyless entry, and fast wifi. Original exposed post and beam construction and Scandinavian-inspired design make for a unique and cozy atmosphere.

Top guest favourite
A modern studio interior features a comfortable leather sofa paired with two armchairs, inviting relaxation. A wooden coffee table with woven placemats sits in front. Soft lighting illuminates the cozy sleeping area, which is set with a spacious bed and tasteful decor, creating a welcoming atmosphere.
Flat in Cooperstown
4.93 out of 5 average rating, 306 reviews

Deer Meadow Farm Studio: spacious studio apartment

Deer Meadow Farm Studio is a modern, open concept Studio apt (24'x16') and includes many amenities to make your stay comfortable and relaxing! Including: WiFi • Spectrum/Apple TV • Radiant floor heat • A/C • Private patio w/ gas grill • All linens/towels • Kitchenette (microwave, mini-fridge, Keurig, toaster). PLEASE NOTE: There is NOT a full kitchen. Located near The Baseball Hall of Fame, Brewery Ommegang, Glimmerglass Festival as well as the many area shops and restaurants!

Superhost
A cozy sleeping area features a queen-sized bed with light bedding and soft throw blankets. A large picture window provides views of the surrounding greenery. The wood-paneled walls and floor create a warm, natural atmosphere, complemented by a small table and a minimalist chair.
Tiny home in Worcester
4.88 out of 5 average rating, 123 reviews

Tiny Home Glamping @ Maia's Place

Enjoy a true Tiny Home Glamping experience at Maia's Place! Located only 20 minutes from Cooperstown and baseball fields. Enjoy beautiful views of the mountains all around. This tiny home sits on a private two acres, has an outdoor patio area for lounging, grilling, and star gazing at night. The inside is fully equipped with a convection stovetop, fridge, bathroom, wifi hotspot, and queen-sized bed with a 5x5 east-facing picture window to capture the perfect sunrise!

Top guest favourite
The exterior of a charming farmhouse is captured, showcasing a green facade with white trim and a red roof. A spacious porch can be seen, providing an inviting entrance. Surrounding grassy areas and trees complement the rural setting, illuminated by natural sunlight.
Flat in Roxbury
4.93 out of 5 average rating, 322 reviews

"Your Country Getaway at Beulah Land Farm."

Enjoy a one bedroom apartment with a private entrance. Head up the old rear staircase around the back of a quaint 100 year old farmhouse. Stairs are a little steep. There is a kitchenette with a two burner stove, sink and under counter fridge. There is one full bath with a shower stall. In the living area there is a day bed with an extra twin mattress underneath. There is wireless internet for your use as well. It is 25 minutes to ski areas.

Guest favourite
A rustic cabin with a green metal roof features a spacious front porch adorned with comfortable seating. Large windows provide ample natural light, and a well-maintained lawn with trees offers a scenic backdrop. The tranquil setting invites relaxation and outdoor enjoyment.
Home in Oneonta
4.92 out of 5 average rating, 111 reviews

Lakefront, family friendly home -Baseball campers!

- Lake/waterfront home on Goodyear Lake. - Conveniently located close to local baseball camps, SUNY Oneonta and Hartwick college - Large lake view patio and yard for games or campfires and lakeside deck and dock. - Enjoy swimming, excellent fishing, and watersports. Canoe, row boat, and pedal boat on site for guests. - Updated spacious home, including a fireplace and air conditioning. - Away from it all, but close to all amenities!

Top guest favourite
The entrance to a rustic cabin is framed by logs, featuring a welcome sign and a seasonal wreath on the door. A pair of wooden rocking chairs sits on a spacious porch, accompanied by a decorative pumpkin and a carved wooden stump.
Cabin in Cooperstown
4.98 out of 5 average rating, 118 reviews

An Upstate NY getaway treasure!

Take it easy at this unique and tranquil getaway. For several hundred years our family has been a part of the Cooperstown community and we look forward to sharing it with you! On over 20 acres of land , you can explore the beautiful landscape of water and woods. Just over the hill from Otsego Lake. Only 3.9 miles (8 min) to Cooperstown’s Main Street in the spring, summer and fall and 5.7 miles (10 min) in winter.

Top guest favourite
The exterior of the A-frame glamp is shown, surrounded by lush greenery and tall trees under a blue sky filled with gentle clouds. A large window reflects the natural scenery, enhancing the connection to nature. The interior view captures a distinctive moon-shaped light fixture suspended from the high ceiling, complementing the triangular architecture.
Place to stay in Oneonta
4.99 out of 5 average rating, 258 reviews

Creekside of the Moon A-frame Cabin

Creekside of the moon A-frame glamp. Float, fish and play in the Catskills. Glamp on the Charlotte Creek in a newly built modern tiny a-frame. Sleep under the full moon. A giant moon light hangs over the bed(s) with a stunning reflection in the window at night over the creekview. Perfect for a romantic getaway, fishing trip, or glamping spot in the Catskills. Close to Cooperstown, NY IG @aframe_moon

Top guest favourite
A serene cabin is nestled amidst a lush green landscape, surrounded by tall trees and vibrant foliage. The charming structure features a blue roof and large windows that offer an inviting appearance. Wildflowers and grasses frame the view, enhancing the peaceful setting.
Cabin in Jefferson
5 out of 5 average rating, 505 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.

Top guest favourite
An open-concept kitchen and dining area is displayed, featuring a large island with seating for four. Sunlight fills the space through multiple windows, illuminating the dining table with chairs. Modern appliances and a light color palette create a bright and welcoming environment.
Home in Milford
4.97 out of 5 average rating, 273 reviews

Creekside: Cozy Cooperstown Retreat

Welcome! Creekside is a ranch style home overlooking a scenic pond. It is a 3 bedroom, 2 bath home with cathedral ceilings and a beautiful open concept feel. If your group would like to spread out, we have an option to add a 4th bedroom and living space with a basement apartment option. Decks on both the front & back of the home let you enjoy all the surrounding nature.

Popular amenities for Maryland family-friendly rentals

When is the best time to visit Maryland?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$229 SGD$393 SGD$242 SGD$242 SGD$343 SGD$427 SGD$452 SGD$418 SGD$338 SGD$320 SGD$242 SGD$295 SGD
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Quick stats about holiday rentals that are family-friendly in Maryland

  • Total holiday rentals

    Explore 40 holiday rentals in Maryland

  • Nightly prices starting at

    Maryland holiday rentals start at $104 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,180 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    40 of Maryland holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Maryland rentals

  • 4.8 Average rating

    Maryland stays are highly rated by guests – averaging 4.8 out of 5!