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Family-friendly holiday rentals in Maryland

Find and book unique family-friendly homes on Airbnb

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 $182 AUD per night before taxes and fees

  • Verified guest reviews

    Over 1,270 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Maryland holiday rentals include Wi-Fi 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!

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
Cabin in Jefferson

Experience a Catskills Lodge

Our modern log home is set up with fine things like Turkish towels, local artisan soaps & the softest sheets. The tasteful decor has an mcm vibe w/industrial touches. Wander outdoors, swim, follow a creek, slip into the forest, hike back, cook dinner in a state of the art kitchen w/ a pantry full of fun gadgets. Relax by the fireplace, sit outside & watch the stars, light a fire. We provide blankets & wood. A welcome basket & a fully stocked coffee bar for the early mornings are waiting for you.

4.98 out of 5 average rating, 216 reviews
Top Guest favourite
The farmhouse features a two-story wooden exterior, accented by vibrant autumn foliage. A decorative entrance with a porch is flanked by shrubs, and an American flag is displayed prominently. Expansive windows offer views of the surrounding landscape, enhancing the home's connection to nature.
Farm stay in Stamford

1820's Farmhouse 182 acres/Private Swimming Pond

Oak Hill Farm c1824, this farmhouse has been fully renovated with a modern take on upstate luxury. Situated on 183 acres of its own land, the house has views across the valley, spring fed swimming pond and a private mountain top. Enjoy morning strolls through our open hay fields, cookout on the covered deck with a wood burning smoker, gas grill, fire pit. Mowed trails through the hay fields, large pathways that are for hiking, foraging, wild life sighting. Air conditioning throughout the house.

4.98 out of 5 average rating, 110 reviews
Top Guest favourite
A spacious bed adorned with white linens sits against a wall featuring a decorative tree of life design. Soft lighting is provided by wall sconces on either side. A decorative pillow adds a touch of comfort, with a bedside table displaying a clock and additional items.
Apartment in Cooperstown

The Carriage House at Arran Fell Farm

A slice of heaven 7 miles from Cooperstown 16 min from Cooperstown Dreams Park.Immaculate,quiet, peaceful working rescue farm. Come and unwind and sleep in the hammock.Large firepit,outdoor games,animal interaction. Complimentary free range eggs, oj, butter, bagels,cream ,coffee and tea provided. Outdoor gazebo with bbq grill.Pick your own veggies when in season. Hike the trail or take a paddleboat or canoe on the pond. Try some fishing, interact with rescue animals. One of a kind experiences.

5.0 out of 5 average rating, 185 reviews
Top Guest favourite
A view from a private porch showcases a spacious green yard surrounded by trees. A storage shed is visible in the background, with a basketball hoop nearby. The intricate white railing features a nature-inspired design that complements the serene outdoor surroundings.
Home in Schenevus

Main Street in the Mountains. See sights & scenery

Enjoy nature: hiking, fishing, (backyard creek/nearby lake) or enjoy the sights. Located 20 minutes from Cooperstown, Oneonta, & Cobleskill. Be moments from local attractions: Baseball Hall of Fame, Farmer's Museum, & more like local breweries (Ommegang), baseball camps; Dreams Park/All Star Village, colleges: Hartwick, SUNY Oneonta, & SUNY Cobleskill, & Bassett Healthcare locations. If staying in, there's high speed internet, streaming channels, washer & dryer, private porch, & access to yard

4.94 out of 5 average rating, 107 reviews
Top Guest favourite
A scenic view of Cooper Creek's property is captured, featuring a rainbow arching over green fields and trees. Various buildings, including the main house, are visible in the background against a backdrop of soft blue skies and hints of clouds.
Home in West Oneonta

Cooper Creek

Cooper Creek is a valuable piece of central New York history that was built in the late 1700s. This homestead once included an outhouse, a spring house, a Cooper shed, and a proud hand hewn timber barn. Robby and Eileen Robbins purchased the property in 1984-finding it in desperate need of plumbing, electricity, as well as emergent repairs in order to preserve as much history as possible. The 18th century beams,& the wooden pegs used instead of nails helps it maintain its unique identity.

4.98 out of 5 average rating, 193 reviews
Top Guest favourite
Cabin in Walton

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.

4.95 out of 5 average rating, 266 reviews
Guest favourite
The A-frame cabin is framed by vibrant autumn foliage, featuring warm lighting that highlights its contemporary exterior design. A spacious wooden deck is furnished with seating and a dining area, overlooking a manicured lawn. The surrounding trees display a palette of orange and yellow leaves.
Cabin in Stamford

The A-Frame at Harvest Moon Acres

Escape to this cozy, pet friendly Aframe tucked in the mountains - perfect for a peaceful getaway surrounded by nature with fireplace and mountain views in Stamford, NY, where the beauty of the Catskill Mountains surrounds you. Whether you’re sipping coffee by the fire, exploring nearby trails, or unwinding under the stars, the cabin is designed for comfort, relaxation and a little adventure Close to scenic hiking trails and nature spots. Short drive to local coffee shop and cafe.

4.97 out of 5 average rating, 328 reviews
Top Guest favourite
A cozy bedroom features a spacious bed layered with a light-colored blanket. Natural light filters through large windows adorned with light curtains, illuminating the room. A stylish rug adds texture to the hardwood floor, while modern pendant lights hang from the ceiling.
Home in Worcester

Tranquil Countryside Escape

Relax with the whole family at this peaceful house in the countryside of New York. A newly renovated 3 bedroom with an expansive yard gives you plenty of space to have fun both inside and outside. Nestled between the mountains the surrounding towns allow for plenty of outdoor activities for all to enjoy. We are also only a 30 minute drive to Cooperstown and the famous baseball hall of fame. Come experience the serentiy and opportunities that this house/location have to offer!

4.91 out of 5 average rating, 106 reviews
Guest favourite
A geodesic dome is situated amidst expansive green pastures, surrounded by rolling hills and trees. The outdoor dining area with lounge chairs and a firepit can be seen adjacent to the dome, offering a scenic view of the countryside.
Dome in Cobleskill

Dome on Agroforestry Farm w/ Mountain View & Ponds

Welcome to The Dome on Long Future Farms! Our unique lodging is designed to provide a relaxing experience for 2-4 guests, with a focus on minimizing our environmental impact and supporting local ecological farming. (There are currently NO animals on the farm, as this is primarily a nut tree farm.) Our dome offers a breathtaking view of our 171-acre agroforestry land, hills and ponds, allowing you to truly connect with the natural beauty of the region.

4.95 out of 5 average rating, 146 reviews
Guest favourite
A porch area is visible, featuring a pair of chairs and seasonal flower decorations in pots. The entrance is adorned with potted plants, while the façade of the building displays wooden siding and multiple windows. A yard with greenery is seen in the background.
Apartment in Cooperstown

One Bedroom Apt Near Dreams Park and Hall of Fame.

The apartment has one bedroom with queen bed, a bathroom, living room/ kitchen, a cott, and WiFi. We're located on 2 rivers, in a beautiful scenic valley near Cooperstown, 5 miles from Dreamspark, and one minute to the Cooperstown Train, which offers various themed rides as well as hand carts. We're 3 miles from famous Ommegang, and 2 other breweries! 20 miles south is Hanford Mills, an authentic 19th century water powered factory!

4.77 out of 5 average rating, 158 reviews
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

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. Row boat on site for guests. - Updated spacious home, including a fireplace and air conditioning. - Away from it all, but close to all amenities!

4.9 out of 5 average rating, 122 reviews
Superhost
The exterior of a spacious cabin is displayed, featuring a dark green facade with large windows and a porch adorned with planters. A gravel driveway leads to a two-car garage, surrounded by lush greenery and tall trees in a serene setting.
Home in East Meredith

Catskills Luxury Cabin

A breathtakingly pristine luxury cabin on 14 private acres, tucked away in an oasis of trees, this is the perfect getaway for barbecues on the back deck, hikes, fishing, enjoying bottles of wine by the fire, and allowing the quiet nature noise to lull you to sleep. Area attractions include: Farmer's Markets, Brushland Eating House, Wayside Cider, New York Safety Track, Antiquing, Hiking, Lakes, Ski Resorts...

4.96 out of 5 average rating, 143 reviews

Popular amenities for Maryland family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top Guest favourite
A firepit surrounded by five wooden chairs is positioned on a gravel area, offering expansive views of the rolling hills at sunset. String lights above enhance the ambiance as the sky transitions into warm hues of orange and purple.
Home in Jefferson

Catskills Mountaintop House w/ HOT TUB and VIEWS!

5.0 out of 5 average rating, 147 reviews
Top Guest favourite
A spacious living area features a high A-frame ceiling with large triangular windows, allowing for abundant natural light and scenic views. A wood-burning stove sits in the center, surrounded by elegant seating arrangements on a plush area rug, enhancing a cozy atmosphere.
Cabin in Margaretville

Modern & Chic Log Home-Spectacular Mountain Views!

4.98 out of 5 average rating, 470 reviews
Guest favourite
A private hot tub is set against a backdrop of lush greenery and rustic wooden panels. Soft lighting illuminates the area, creating a calming environment. A wooden bench is positioned nearby, further enhancing the serene setting.
Farm stay in Harpersfield

Three Willows | Pond, Sauna & Treehouse Retreat

4.94 out of 5 average rating, 138 reviews
Guest favourite
Cabin in Franklin

The Roost | Catskill Retreat - 7 Acres + Hot Tub

4.97 out of 5 average rating, 159 reviews
Guest favourite
A modern cabin design features broad wooden slats and floor-to-ceiling glass doors. A spacious deck includes loungers and a hot tub, surrounded by lush greenery, enhancing the outdoor aesthetic. Soft lighting illuminates the seating area, creating a welcoming environment.
Home in Hunter

Modern House with Mountain View @Getawind

4.96 out of 5 average rating, 230 reviews
Guest favourite
An open-concept living space showcases a modern kitchen with granite countertops and stainless steel appliances. A dining area features white chairs around a wooden table, while a cozy sofa is positioned in the living area, complemented by wooden accents and natural light.
Cabin in Laurens

Luxury Catskills Log Cabin Lakeside Hot Tub, Boats

4.94 out of 5 average rating, 200 reviews
Guest favourite
An A-frame cabin is nestled among trees, with a metal roof and wooden deck. An outdoor fire pit, surrounded by stone, features several dark chairs arranged invitingly. The natural setting is enhanced by vibrant autumn foliage, providing a tranquil retreat atmosphere.
Cabin in Stamford

A-Frame on Pudding Hill | Hot Tub + Outdoor Shower

4.95 out of 5 average rating, 219 reviews
Guest favourite
An aerial view showcases a modern dome structure on a spacious property, illuminated against the night. Surrounding pathways are lined with lights, enhancing the serene outdoor setting. Nearby, a tent with soft lighting hints at an inviting gathering space.
Dome in Hobart

Mtn View Lux Dome w/ Heated Plunge Pool

4.92 out of 5 average rating, 247 reviews

Family- and pet-friendly home rentals

Top Guest favourite
The cottage features a spacious covered porch with white railings and steps leading to the yard. Two chairs are positioned near the entrance, and the exterior is complemented by a light-colored facade. Lush greenery surrounds the property, contributing to a serene outdoor setting.
Cottage in Milford

At Home Base Yellow Cottage

4.99 out of 5 average rating, 155 reviews
Top Guest favourite
The light-filled studio apartment features a spacious bed with a white comforter, a glass-topped table, and two brown chairs. A potted plant is positioned near the window, which provides natural light. A minimalist clothing rack is visible in the corner, contributing to the open feel.
Holiday home in East Meredith

Succurro : Studio

4.95 out of 5 average rating, 298 reviews
Top Guest favourite
A garden brimming with vibrant orange flowers is set in front of a dark structure. A red building is visible in the background, surrounded by lush trees, adding to the green landscape. This serene outdoor space emphasizes a natural and welcoming environment.
Bungalow in Margaretville

The Porch Upstate Super clean

4.96 out of 5 average rating, 385 reviews
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

Creekside of the Moon A-frame Cabin

4.99 out of 5 average rating, 339 reviews
Top Guest favourite
A serene landscape is presented with rolling green hills under a clear blue sky. The glowing sun rises on the horizon, illuminating the dewy grass and trees. Fenced areas and distant hills contribute to the peaceful atmosphere of the mountain top.
Farm stay in Conesville

6 Bedroom 1860 Farmhouse Mountain Views Windham

4.99 out of 5 average rating, 107 reviews
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

Romantic Cozy Cabin with a View of the Wetlands

4.99 out of 5 average rating, 213 reviews
Top Guest favourite
The 1870 farmhouse showcases a white exterior with detailed porch railings and a front porch. A small flag is displayed, while lush green grass surrounds the home. The beautiful landscape features trees and rolling hills in the background, emphasizing the peaceful country setting.
Home in East Meredith

Grace House

4.96 out of 5 average rating, 136 reviews
Guest favourite
Home in South Kortright

Inez's Studio

4.9 out of 5 average rating, 555 reviews

Family-friendly home rentals with a pool

Superhost
Cabin in South Kortright

Contemporary Cabin w/ Hot Tub, Lake & Fireplace

4.89 out of 5 average rating, 309 reviews
Guest favourite
A seasonal saltwater pool is surrounded by a wooden deck and lounge chairs, offering a scenic view of the lush hillside. An umbrella provides shade, and a basketball hoop is positioned at one end of the pool, enhancing outdoor leisure options.
Cabin in Town of Shandaken

Catskills Retreat | Heated Pool & Hot Tub

4.95 out of 5 average rating, 247 reviews
Top Guest favourite
A wooden hot tub is situated on a spacious deck, offering views of rolling hills and a blue sky dotted with clouds. The bubbling water reflects the sunlight, creating a serene atmosphere conducive to relaxation and enjoyment of the surrounding natural landscape.
Home in Delhi

Catskills Barn Apt with MTN views on 34 acres

4.88 out of 5 average rating, 318 reviews
Top Guest favourite
A modern cabin stands against a backdrop of lush greenery and mountains. Large windows invite natural light, while a deck with seating is visible in the foreground. Surrounding landscaping includes trees and shrubs, creating a serene and private outdoor space.
Cabin in Arkville

Hike & Sauna! Modern Mountain Escape

4.98 out of 5 average rating, 173 reviews
Guest favourite
The image features a modern hot tub in the foreground, with bubbling water and a clear dome structure nearby. The dome showcases a seating area surrounded by nature, with trees visible in the background against a bright blue sky.
Chalet in Prattsville

White Holiday Cozy Chalet Pool/Hot Tub/bubble room

4.9 out of 5 average rating, 133 reviews
Guest favourite
An above ground pool is situated in a spacious yard surrounded by lush greenery. The pool's clear blue water reflects the sky, while a nearby patio area is equipped with seating and umbrellas. A charming red house serves as a backdrop, completing the serene outdoor scene.
Home in Windham

Catskill Villa | 6BDRM, Pool, Hot Tub & Movie Room

4.95 out of 5 average rating, 108 reviews
Guest favourite
A spacious deck features two comfortable chairs and a round table at its center, offering a clear view of the expansive Catskill Mountain landscape. Lush greenery and rolling hills stretch into the distance under a bright blue sky.
Home in Stamford

Hawk View

4.97 out of 5 average rating, 148 reviews
Top Guest favourite
Chalet in Jewett

Secluded Catskills Retreat w/ Hot Tub & Views

4.97 out of 5 average rating, 193 reviews

When is the best time to visit Maryland?

MonthJanFebMarAprMayJuneJulyAugSeptOctNovDec
Avg. price$320 AUD$292 AUD$273 AUD$343 AUD$442 AUD$459 AUD$484 AUD$448 AUD$362 AUD$346 AUD$327 AUD$371 AUD
Avg. temp-4°C-3°C2°C9°C15°C20°C23°C22°C18°C11°C5°C-1°C

Destinations to explore