Family-friendly vacation rentals in Cumberland

4.97 out of 5 average rating, 155 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, 272 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.

4.78 out of 5 average rating, 170 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, 521 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, 230 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, 125 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 !

4.94 out of 5 average rating, 232 reviews

A charming two-story house is surrounded by well-tended gardens, featuring a gravel driveway leading up to the front porch. The exterior is painted in a soft gray hue, complemented by large windows that offer opportunities for natural light.

Home in Frostburg

Country Home Near Main St. & Trail

Welcome to this charming and cozy home sitting at the highest point in Frostburg. Incredible mountain and forest views from the upstairs windows, lots of old house details and including two staircases and a sleeping porch. There are hardwood floors throughout. Lots of space to relax. Two full baths, one with shower and one with tub/shower. Gas range and fully stocked kitchen. Smart TV's in two bedrooms, and in the main living room. Strong Wifi, and a washer and dryer in the basement.

4.84 out of 5 average rating, 167 reviews

A corner view of the charming brick facade of the house is captured, featuring a white door adorned with glass panels. The rich pink color of the brick is complemented by green foliage overhead. A lantern is positioned beside the door, creating a welcoming entryway.

Home in Cumberland

Charming 1907 Home in Historic Downtown Cumberland

This charming 1907 home is located just blocks from the main pedestrian street in Historic Downtown Cumberland and a 10 minute walk from Canal Place, the C&O Canal Great Allegheny bike trails, and the Western Maryland Scenic Railroad. The remodeled interior is equipped with all the modern conveniences, including a large kitchen and bathroom with large tub and seven-head shower. The house maintains its historic charm with exposed brick and has a balcony, back patio, and yard space.

4.9 out of 5 average rating, 178 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, 563 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, 323 reviews

A modern kitchen features light gray cabinetry with an island centerpiece. Stainless steel appliances, including an oven and refrigerator, are complemented by a colorful bowl display. A detailed wall graphic provides helpful kitchen rules, while ample counter space offers convenience for meal preparation.

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, 130 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.

Popular amenities for Cumberland family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

5 out of 5 average rating, 144 reviews

The treehouse is elevated among bare branches, featuring a large deck with seating. Warm lighting highlights the wooden exterior, and expansive windows provide views of the surrounding forest. Steps lead down to the ground, enhancing accessibility to the natural setting.

Treehouse in McHenry

Bird's Eye View

4.95 out of 5 average rating, 154 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, 233 reviews

Cabin in Great Cacapon

Walk in the clouds Cabin

4.94 out of 5 average rating, 119 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

Camper/RV in Capon Bridge

4.97 out of 5 average rating, 321 reviews

Large Glamper w/ Hot Tub & full bath, amazing view

4.99 out of 5 average rating, 236 reviews

A private deck offers a cozy gas fire pit surrounded by inviting seating. The hot tub is visible, with expansive views of the colorful autumn landscape stretching across the horizon. Soft clouds linger above the serene scenery.

Treehouse in Swanton

The Overlook; A Romantic Treehouse for Two

4.97 out of 5 average rating, 196 reviews

A hot tub is positioned under a covered porch, featuring bubbling water and a soothing green light. In the background, the tranquil Cacapon River is visible, surrounded by autumn foliage. A fire pit can be seen nearby, contributing to the relaxing outdoor ambiance.

Cottage in Capon Bridge

The 3R's River, Relaxation, Retreat + hot tub

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, 138 reviews

Yoder School Guest House with wifi and hot tub

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 164 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, 114 reviews

A cabin features a covered front porch with steps leading up to the entryway. The exterior walls are painted in a muted green color. Surrounding landscaping includes a gravel walkway and freshly mulched flower beds, set against a backdrop of trees and open grass.

Tiny home in Mount Storm

New 1-bedroom tiny cabin with fireplace

4.95 out of 5 average rating, 103 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

4.87 out of 5 average rating, 685 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, 127 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, 279 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

4.91 out of 5 average rating, 258 reviews

The exterior of a single-family house is shown, featuring a light gray facade and a welcoming yellow front door. An American flag flutters above the steps, which are bordered by colorful flower pots. A well-maintained lawn complements the inviting entrance.

Home in Meyersdale

Our House on the GAP Bike Trail

4.9 out of 5 average rating, 202 reviews

A charming cottage is shown nestled in a snowy landscape. The exterior features wooden siding and two balconies that provide access to the home. Surrounding trees are visible, along with a clear blue sky overhead, creating a serene winter scene.

Cottage in Oakland

Pet friendly-Cottage in the Woods

Family-friendly home rentals with a pool

4.94 out of 5 average rating, 261 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

The living area displays a warm, inviting space with a plush sectional sofa and a round coffee table centered on a patterned rug. A wooden dining table is visible in the background, surrounded by chairs. Natural light enters through windows, enhancing the cozy atmosphere.

4.97 out of 5 average rating, 109 reviews

Cedar Loft at The Woods-Vintage Chic Cabin Retreat

5 out of 5 average rating, 105 reviews

A circular fire pit is surrounded by six gray Adirondack chairs, set on gravel. Beyond, a spacious wooden deck is visible, featuring a covered area and a picnic table. The yard is fenced with trees providing a natural backdrop.

Home in Hedgesville

Spacious & Charming! Large deck+Game shed+Firepit

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, 283 reviews

Bear Pines Retreat ~ Game Room ~ Screened Porch

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, 102 reviews

Cozy A-Frame Cabin In The Woods

4.98 out of 5 average rating, 264 reviews

The living area features a modern design with a gas fireplace as the focal point. A chandelier hangs from the vaulted ceiling, illuminating comfortable seating arrangements. Large windows offer a view of the wooded landscape, while a TV is mounted on the wall, providing entertainment options.

Guest suite in Accident

New! The Butterfly Suite at Enchanted Table Meadow

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.

4.88 out of 5 average rating, 129 reviews

Five Oaks Cabin at The Woods Resort

Aerial view showcases a cabin nestled amid a vast expanse of lush green forest. The treetops create a vibrant, uninterrupted canopy, with distant mountain peaks visible under a clear sky, emphasizing the cabin's serene and secluded location.