Vacation rentals in Cumberland

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.

4.93 out of 5 average rating, 262 reviews

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.

The front entrance features a bright blue door framed by cheerful yellow accents. The pathway leads to the porch, surrounded by manicured green grass and decorative potted plants. A tree with vibrant red leaves adds a touch of color and depth to the scene.

5 out of 5 average rating, 115 reviews

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.

4.99 out of 5 average rating, 487 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.

5 out of 5 average rating, 115 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 !

4.99 out of 5 average rating, 186 reviews

A blue cottage is illuminated at night, showcasing distinct architectural features including gabled roofs and decorative trim. The background reveals a sprawling view of the city lights, creating a contrast against the dark sky. Trees and greenery frame the scene, enhancing the serene atmosphere.

Cottage in Cumberland

The Cottage on the Hill

Nestled against a hillside, at the end of a small city lane, sits a charming private retreat. Park in one of your reserved spaces and step down to a unique retreat high above the city to enjoy a vintage cottage with modern amenities. Walk to Historic Cumberland, enjoy local and regional attractions, or stay in and grill, build a fire, or play pool, poker, board or yard games. Well appointed, fully equipped, and with a beautiful view, come relax and enjoy this one of a kind location.

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.

4.84 out of 5 average rating, 160 reviews

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.

4.96 out of 5 average rating, 242 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

Tired of the chaos and need a place to unwind and relax ? We have the perfect place for you! A quaint, quiet cabin to let you clear your mind and spirit after a day of hiking, biking or kayaking since we are only five miles from both the Paw Paw tunnel and the Potomac river. The cabin is equipped with electric, heating, stove top, microwave, large deck, hammock chairs, horseshoe pit, 2 double size futons with room to spare, indoor toilet but BEST of all is showering outside!

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.

4.9 out of 5 average rating, 550 reviews

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.

A charming outdoor seating area features two intricately designed white wicker chairs with floral cushions and a small table. Soft string lights enhance the space, while a lush green view is visible in the background through the open area.

4.91 out of 5 average rating, 117 reviews

Queen City Quarters- cozy, historic, 1920s home

Stay in a quiet setting as you explore Cumberland, MD. Enjoy a day trip on the nearby, scenic, steam train. Bike the Gap and C&O trail, minutes away. Explore the restored historic downtown with shopping and restaurants. This space is not suitable for small children or those with mobility concerns. No large groups or parties. Bedroom doors are louvered doors. See pictures. Research city and area if you are unfamiliar with economic conditions. We have a bike rack for 3 bikes.

4.86 out of 5 average rating, 310 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.

4.98 out of 5 average rating, 135 reviews

A single-story house is depicted surrounded by lush green trees, set against a backdrop of rolling hills. The exterior features a metal roof and a front porch, with a driveway leading to a garage. A spacious yard is visible, providing a serene countryside setting.

Home in Artemas

Rines' Country Getaway

county setting, rolling hills, quite, great place to get away from hi tech.Beautiful sunrises and sunsets. Fresh air. Take a long walk in the country side. Great front and back yard, Maybe able to catch glimpse of local wildlife or local farmers working the fields. Located 20 to 30 minutes from Everett,PA to the north, Cumberland, MD to the west, Hancock,MD to the east and the Potomac River to the South. 10 minutes from Interstate 68.

4.93 out of 5 average rating, 149 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.

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for Cumberland vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Cumberland

5 out of 5 average rating, 27 reviews

A well-appointed living area features a plush sofa with blue accent pillows and a dark coffee table. A round dining table is visible, accompanied by chairs, while a modern kitchen with bar seating can be seen in the background. Natural light flows through large windows.

Home in La Vale

CJ’s Escape Great location & just like home

5 out of 5 average rating, 12 reviews

A single-story home with a red metal roof is framed by well-maintained green lawns. Window awnings provide shade, while a concrete walkway leads to the front porch, offering access to the inviting entrance. Trees and landscaping are visible in the surrounding area.

Home in La Vale

616 Mountain Suite

4.91 out of 5 average rating, 11 reviews

The historical home is highlighted against a twilight sky, with porch lights illuminating a welcoming entrance. A well-maintained lawn, bordered by shrubs and flowers, frames the pathway. The upper balcony features comfortable seating, inviting relaxation while enjoying the serene landscape.

Guesthouse in Cumberland

The Villa

Superhost

A living room area features soft, striped upholstery on a graciously curved sofa alongside a wooden armchair with a vibrant red cushion. An ornate coffee table holds fresh fruit. A decorative fireplace with candles and an artistic wall display adds an elegant touch to the space.

4.72 out of 5 average rating, 61 reviews

The Cumberland Trail House - Near GAP/C&O Canal

The living room features a comfortable seating area with floral-patterned upholstery and rustic wooden tables. Large windows allow natural light to fill the space, complemented by elegant curtains. A ceiling fan provides airflow, while decorative accents enhance the homely ambiance.

4.91 out of 5 average rating, 56 reviews

Cozy Cottage

4.97 out of 5 average rating, 75 reviews

A bright living room features a turquoise sectional sofa complemented by patterned accent chairs. An area rug with intricate designs covers the floor. Light is provided by large windows, while decorative mirrors and wall art add visual interest to the space.

Apartment in Cumberland

BlueSideUp! Comfy, light filled, eclectic, retreat

Superhost

A living area is presented with a grey sofa adorned with patterned cushions. A wooden coffee table sits in front, with three candles arranged on top. A flat-screen TV is mounted on a stand, and a door leads to the outside, complemented by warm light filtering through the window.

Apartment in Cumberland

4.82 out of 5 average rating, 17 reviews

Lovely 1bed unit in the hills of Western Maryland

A wooden sauna, designed in an oval shape, is situated on a wooden deck. Adjacent hot tubs are visible, while a grill rests nearby. The background shows a house and greenery, with sunlight illuminating the area.