Family-friendly holiday rentals in Cumberland

4.98 out of 5 average rating, 167 reviews

A cozy living area features wooden paneling and a stone fireplace with an active flame. Two deer heads are mounted on the wall. A television is positioned above the fireplace, and small evergreen trees add a touch of nature to the space.

Guesthouse in Fairhope

Mountain View Acres Getaway

Enjoy nature in a beautiful peaceful setting with 100 acres of privately owned property. Breathtaking panoramic views spanning 45 miles in a tranquil natural spot with hiking trails throughout. Handicap accessible. Within a short drive of 2 major ski resorts, the Flight 93 Memorial and 2 wineries. Several restaurants and a brewery also within a 15 minute drive. The property includes an outside firepit that is a favorite place for guests to relax and enjoy the breathtaking views of the mountains.

4.93 out of 5 average rating, 277 reviews

A Cape Cod style cottage is depicted, featuring a porch with a sloped roof and a welcoming entrance. The surrounding yard is green, bordered by neatly trimmed shrubs. In the background, rolling hills are visible, providing a natural setting.

Home in Cumberland

Jacob's Cottage

Free WI-FI now available. Our place is good for couples, solo adventurers, business travelers and families (with kids). The Cottage is a quaint, Cape Cod style house built in 1950. It sits high on a hill in the heart of Maryland's Appalachian Mountains in Allegany County. It is surrounded by views of Wills Mountain and Shrivers Ridge. The Cottage sits amongst a 660 acre family managed forest. Visitors have spotted deer, turkey, rabbits, squirrels, black bear and a multitude of song birds.

5 out of 5 average rating, 129 reviews

Home in Cumberland

NEW LISTING-"Cumberland Cottage"-charming,quaint

Relax in this charming, renovated rancher in a peaceful setting. Located outside of the city limits but convenient to attractions and dining. This home is comfy with all the amenities you have in your own home. Outside area for your children to play or for you to relax on the back porch. Cumberland is in easy driving distance to PA and WV. Enjoy cooking together and dining or playing games in the dining room, then relaxing in the living area. Renovated but still keeping the charm of a rancher.

4.78 out of 5 average rating, 171 reviews

A cozy seating area features a light-colored sofa, complemented by a red accent pillow. A glass coffee table is positioned nearby, with a round dining table and four white chairs visible in the background. The kitchenette area is furnished with essential appliances and wall art is displayed on the whitewashed walls.

Apartment in Cumberland

The Caverne'-quaint EFF near C&O Canal, GAP & UPMC

This special place is close to everything Cumberland offers making it easy to plan your visit. Just minutes via bike to GAP and C&O Canal. This serviced apartment includes all the amenities a hotel room offers but with privacy and extra space. Off street parking is just steps away from the space where amenities include coin operated laundry & soda machine. Free wifi, tv, full size refrigerator, coffee maker with coffee etc provided, and micro & toaster oven for quick snacks or simple meals.

4.99 out of 5 average rating, 545 reviews

A spacious bedroom is furnished with a wooden bed featuring a patterned quilt. Soft lighting is provided by two bedside lamps. A small window is dressed with a plant on the sill, allowing natural light to brighten the inviting space.

Apartment in Cumberland

Steeple View Flat in Historic District

Relax in your first level flat. Entire private efficiency suite with a secure self check in. The entrance located along side of the main house in Cumberland’s Historic District. You can safely park your car and walk to many of Cumberlands amenities. If you’re biking, they can be stored inside. Canal Place has unique shops a winery and a bike rental facility. Cumberland theater is adjacent to the property, also Baltimore St. Promenade offers a delicious choice of indoor and outdoor dining.

4.97 out of 5 average rating, 242 reviews

A cozy living area features a spacious sectional sofa adorned with a colorful throw. Natural light streams through multiple windows, illuminating the warm beige walls and soft carpet. An antique wooden table and a vintage chair add character to the inviting space.

Apartment in Meyersdale

Country Home

Relax with family, friends, or enjoy a solo retreat at this peaceful place to stay in the country. Chestnut House was built in the early 1940s, with Wormy Chestnut wood everywhere! It is a unique home, with an apartment built over a garage / wood working shop.. then connected to the main house later. This space available to rent is separate and fully functional from the main house where we live. Enjoy 2 bedrooms, 1 bathroom, full kitchen and living area.. along with the large outdoors!

5 out of 5 average rating, 135 reviews

The exterior of a renovated log cabin is showcased, featuring traditional log and chink construction. A substantial stone chimney rises alongside the cabin. A spacious porch is present, equipped with a couple of white chairs, surrounded by natural greenery and autumnal foliage.

Cabin in Springfield

1832 Historic Washington Bottom Farm Log Cabin

Welcome to our renovated 1832 Log Cabin on the grounds of the George William Washington and Sarah Wright Washington 19th century plantation. The cabin was the first structure built. Then came barns and slaves’ quarters (no longer standing). The dairy barn is now a woodworking shop and the bank barn was recently restored. The main house, built in 1835, is Greek Revival style. Today, our 300+acre is Certified Organic. We border the South Branch of the Potomac River. It’s ALMOST HEAVEN !

4.9 out of 5 average rating, 188 reviews

A cozy living area features a dark sectional couch complemented by a patterned area rug. A small table is positioned beside the couch, and a television rests on a wooden console, creating a comfortable space for relaxation.

Apartment in Frostburg

The GreyLoo

Cozy, clean and friendly downstairs apartment. Stocked with all the things you need for a short stay as well as the long haul. Close to the Great Allegheny Passage, Main Street Frostburg, Frostburg State University, the Frostburg Pool, and many other locations. Located 33 mi from Wisp Resort/Deep Creek Lake and 18 mi from Rocky Gap Casino Resort. Just a few miles from I68. Enjoy this cozy place and bring your furry friends. Lots of nearby hiking, biking, and outdoor adventures.

4.9 out of 5 average rating, 575 reviews

A vibrant red window frame complements the natural light streaming through diamond-shaped panes. A potted plant sits on a wooden shelf beneath the window, alongside wooden signs that read 'WELCOME' and 'Make Some Memories.' A bicycle-themed artwork is displayed nearby.

Home in Cumberland

Cumberland Street House -GAP trail perfection!

Cyclists dream come true! The Cumberland Street House is less than a quarter mile from the Great Allegheny Passage - perfect for large groups! All of Cumberland's charm within walking distance. Downtown restaurants and shops only a half a mile away. Historic district, Cumberland Theatre & Western Maryland Scenic Railroad are just around the corner. Bikes can easily be stowed in the back room off the kitchen. Easy parking, and fenced-in yard is great for kids and pooches.

4.87 out of 5 average rating, 331 reviews

Home in Frostburg

Allegany Connection

NOTICE: extra santizing of hand touching areas in place for your protection. This eclectic 2-story duplex, late 18th century structure has both old and new charm. Single BR & bath upstairs; LR and Kit downstairs. Only 1 block from Main St. restaurants & unique shops. All are welcomed. Please bring your own infant bed. Sorry no pets. Free reserved parking for 1 vehicle & fast Wi-Fi. Instant booking is on. ABSOLUTELY NO SMOKING, or any kind is permitted inside our home.

5 out of 5 average rating, 139 reviews

A spacious living area features a large leather sectional sofa with accent pillows, paired with rustic wooden coffee tables. A sleek entertainment center holds a wall-mounted TV, while framed landscape artwork adorns the walls, adding a touch of color to the room.

Apartment in Accident

The Nest near Deep Creek

Kick back and relax in this calm, stylish space. Brand new, beautiful one bedroom apartment above a detached garage just 5 miles from Deep Creek Lake. Beautifully designed space with craftsman quality large kitchen, king size neo-industrial walnut bed, live-edge vanity and wall cap, articulating lamp, all made by local craftsman. Leather pull out couch with queen bed sleeps two extra guests. Relax by the fire pit and listen to the birds in the woods.

4.95 out of 5 average rating, 202 reviews

A cozy living room is presented with a leather sofa and a rustic coffee table. A traditional bookshelf filled with decor and framed photos is situated against a brick wall. A television is mounted above a brick fireplace, enhancing the gathering space.

Townhouse in Cumberland

The Shadoe on Greene

Just a stones-throw from everything Cumberland has to offer, The Shadoe on Greene is at the heart of it all. Literal steps from the Western Maryland Scenic Railroad, the Great Allegheny Passage trail & the Historic City Center, with a wide array of local shops and eateries. This unique property was built in the 1850's and has been lovingly restored to embrace it's history, as well as provide all of the modern amenities you'd expect.

Popular amenities for Cumberland family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 203 reviews

The unique dome structure is surrounded by lush trees, featuring large windows and a cozy entrance. An inviting outdoor seating area with a fire pit and black chairs is positioned on the wraparound deck, accompanied by a hammock and a hot tub.

Dome in Mercersburg

StayAround Dome ~ Unique & Tranquil Gem ~ Sauna

4.94 out of 5 average rating, 160 reviews

The cabin is illuminated at night, showcasing its rustic charm among surrounding trees. Warm lights accentuate the porch and pathway, enhancing the inviting atmosphere. The outdoor space is highlighted by well-placed rocks and greenery, creating a serene outdoor retreat.

Home in High View

Mtn. View~Cave Hot Tub~50 Ac~ATV Trails~Fishing

4.94 out of 5 average rating, 246 reviews

Cabin in Great Cacapon

Walk in the clouds Cabin

4.99 out of 5 average rating, 102 reviews

An inviting outdoor area surrounds a contemporary chalet, featuring a walkway made of stepping stones and a cozy fire pit area. Seating is provided nearby, and lush greenery frames the property, creating a serene connection with nature.

Cabin in Swanton

Chalet in the Orchard; Romance, Luxury, Relaxation

Cabin in Berkeley Springs

The cabin is nestled among lush trees, featuring a wraparound deck and comfortable seating areas. An inviting entrance leads up wooden steps, with outdoor lighting enhancing the serene atmosphere. A hot tub is visible on the deck, surrounded by greenery.

5 out of 5 average rating, 309 reviews

+ The Cabin + @CPP - Hot Tub- Dog Friendly- View

4.94 out of 5 average rating, 125 reviews

An outdoor space features a hot tub and a seating area with modern chairs surrounding a wood coffee table. The area is nestled among trees, and a stone pathway leads up to a set of stairs leading to the cottage.

Home in Great Cacapon

Hot tub/Pool Table/Wi-Fi/Gym/Views/Pets/Tanning

Superhost

The cabin is nestled among tall trees, showcasing a wooden exterior with a blue metal roof. Surrounding greenery adds a natural touch, while a gravel path leads to the entrance, enhancing the cabin's secluded appearance in a tranquil wooded setting.

Cabin in Green Spring

4.75 out of 5 average rating, 174 reviews

Potomac Cabin - Riverfront, 7 acres, sleeps 14

Guesthouse in Grantsville

A well-appointed kitchen features warm wood cabinetry and a spacious granite countertop. Stainless steel appliances, including a gas range and microwave, are visible. A central island provides additional preparation space, with overhead lighting illuminating the area. Natural light enters from the adjacent room.

4.98 out of 5 average rating, 145 reviews

Yoder School Guest House with wifi and hot tub

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 174 reviews

A cozy living space features a wooden ceiling and light-colored walls. A small electric fireplace is placed beneath a wall-mounted television. A coffee table sits centrally, surrounded by two comfortable chairs and a couch, with a front door visible to the side.

Cabin in High View

Mary's Cabin

4.96 out of 5 average rating, 115 reviews

The exterior of the two-story cottage features a white clapboard façade with black trim. A welcoming front porch, supported by dark columns, offers a partial view of the lush green surroundings and open space nearby.

Cabin in Grantsville

Casselman View Cottage - Washington's Cottage

4.87 out of 5 average rating, 701 reviews

A well-maintained exterior showcases a brick building with a white double door entrance. Surrounding greenery includes manicured lawns and bushes, enhancing the natural setting. The entrance is easily accessible, providing a welcoming approach to the ground-level unit.

Home in Inwood

Arden House, Inwood WV

4.95 out of 5 average rating, 130 reviews

The cabin features a rustic design with wooden siding and a steeply pitched roof. A front porch is visible, and a small set of stairs leads to the entrance. The surrounding yard is grassy, bordered by trees, with a clear blue sky above.

Cabin in Springfield

Secluded 2 BR cabin in the forest awaits you!

4.92 out of 5 average rating, 282 reviews

The cabin features a rustic wooden exterior with a spacious screened-in porch. Surrounded by lush greenery, it includes a visible canoe along the side. A metal trash can stands nearby, emphasizing the natural setting and accessible outdoor area.

Cabin in Great Cacapon

Rustic Cabin on Cacapon River for Private Getaway

4.95 out of 5 average rating, 140 reviews

A charming A-frame cabin is situated on a gravel path, surrounded by tall trees. A deck extends from the upper level, featuring two outdoor chairs. The natural stone border enhances the landscaped area, providing a cozy and inviting outdoor space.

Cabin in Hancock

Secluded two bedroom cabin on 5 acres

Superhost

The cabin is set amidst lush greenery, featuring a wooden exterior and a welcoming front porch with a railing. Flower pots line the porch, and steps lead to the entrance. A gravel pathway and trees surround the cabin, enhancing the secluded atmosphere.

Guesthouse in Berkeley Springs

4.82 out of 5 average rating, 308 reviews

Terrapin Cabin. A sunny, quiet cabin in the woods.

4.96 out of 5 average rating, 261 reviews

A wooden cabin is nestled among tall trees, featuring a dark exterior and a metal roof. A wraparound deck provides an elevated view of the surrounding forest, with large windows allowing natural light to fill the interior.

Cabin in Paw Paw

Easygoing

Family-friendly home rentals with a pool

4.94 out of 5 average rating, 270 reviews

A cozy living area features a dark blue sofa, a coffee table with decorative plants, and a dining table visible in the background. A ladder leads to a loft area with additional sleeping space. Large windows allow natural light to brighten the space.

Condo in Somerset County

Beautiful, 2 bedroom condo

4.95 out of 5 average rating, 149 reviews

A two-story condo building is shown against a clear blue sky, surrounded by well-maintained greenery. The parking area in front features designated spaces, with vehicles parked nearby. Trees provide shade, enhancing the inviting atmosphere of the community.

Condo in McHenry

Lake Access/2BR/2Bath/kitchen/pool/5m to Wisp

The cabin features a contemporary A-frame design with large windows that reflect surrounding trees. A spacious deck wraps around the structure, providing outdoor seating options. Natural light streams through the windows, inviting a connection with the outdoors.

4.93 out of 5 average rating, 293 reviews

Bear Pines Retreat ~ Game Room ~ Screened Porch

4.97 out of 5 average rating, 218 reviews

A spacious sleeping area features a large bed adorned with a quilted cover and decorative cushions. A wooden accent wall with soft lighting complements the neutral decor. A window framed by dark curtains offers a view of the outdoor greenery, enhancing the room's inviting atmosphere.

Guest suite in Accident

New! The Board Room at Enchanted Table Meadow

The living area features large two-story windows that offer views of the surrounding wooded landscape. A cozy leather sofa and armchair are complemented by a wooden dining table with seating for six. Warm lighting and natural textures enhance the inviting atmosphere.

5 out of 5 average rating, 110 reviews

Cozy A-Frame Cabin In The Woods

5 out of 5 average rating, 106 reviews

An inviting living area features a large, comfortable sofa with warm-toned cushions, situated near a stone fireplace. Exposed wooden beams adorn the ceiling, while natural light streams through doors leading to an outdoor space. A dining table and rustic decor complement the cozy ambiance.

Condo in Champion

Sleeps 6, 2BR, 3BED, FREE Shuttle, POOL, Hot Tub

A charming cabin is nestled among lush trees, featuring a spacious deck that overlooks the surrounding greenery. The structure highlights a gabled roof and large windows, inviting natural light into the house. The forested setting enhances the feeling of seclusion and tranquility.

4.87 out of 5 average rating, 137 reviews

Five Oaks Cabin at The Woods Resort

A gravel area features several rustic wooden chairs arranged around a stone fire pit, with a gentle fire burning. Soft string lights illuminate the space, enhancing the cozy atmosphere. The exterior of the cabin is visible in the background, surrounded by trees.