Vacation rentals in Cumberland

4.97 out of 5 average rating, 144 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.

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, 266 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.

Bungalow in Great Cacapon

A spacious deck features a round table surrounded by six metal chairs, shaded by a green umbrella. Potted plants and flowers add greenery, while a small American flag sits among the foliage. The trees provide a natural backdrop, creating a tranquil outdoor space.

4.9 out of 5 average rating, 572 reviews

Rooster Wrest in the Trees

Sweet 2 bedroom bungalow. Cozy, ideal for lovers, or a quiet beautiful somewhat rustic retreat environment. Rooster has 1 full bath. Living room with satellite TV, Netflix; wood burning stove fireplace, wood provided, fully equipped kitchen, dining table, linens and starter paper goods furnished. Large deck and screen porch looking out on Cacapon Mountain. Hot tub off master bedroom deck in trees, feels like a tree house. Many mornings mist rises up from river, half mile away as crow flies.

5 out of 5 average rating, 119 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, 503 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, 120 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 !

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.

4.85 out of 5 average rating, 164 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.

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, 558 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.

4.84 out of 5 average rating, 134 reviews

The cabin features a warm wooden facade and a spacious front porch with rocking chairs, providing an inviting outdoor space. Sunlight filters through the trees, illuminating the surroundings, while the raised deck offers a view of the natural landscape.

Cabin in Fort Ashby

Hilltop Cabin Retreat - Secluded & cozy - Wi-Fi!

The Sonny Side Hilltop 10-acre Cabin is the perfect secluded getaway to unwind and enjoy nature. Spend quality time with friends/family, explore the outdoors, ATV trails, or hunt with appropriate tags - contact for more details. My father (Sonny) built this cabin in 2004 with his own two hands. It was his primary residence until passing from cancer at my sister's home in Maryland in 2019. We would like to share this lovely cabin with guests to help offset costs. Please Enjoy!

4.98 out of 5 average rating, 104 reviews

The cottage is nestled among vibrant autumn foliage along the riverfront. A rock cliff rises behind it, while a winding path leads to the house, which is surrounded by a mix of colorful trees. The serene river can be seen nearby.

Cottage in Green Spring

The River House

A cozy, spacious and private get away with access to entire finished house. Located river front of the South Branch of the Potomac River, giving it the best view in the area. This cottage is also within 3 miles of C&O Canal, 17 miles from Historical Romney, 15 miles to Cumberland, MD and 10 miles to the Paw Paw, WV tunnel. 2 kayaks and 1 canoe available for river excursions. Come enjoy hiking, biking, kayaking, fishing or simply soak in all nature has to offer in the backyard.

4.87 out of 5 average rating, 313 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.

4.93 out of 5 average rating, 165 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

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Popular amenities for Cumberland vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Boutique hotels in Cumberland

4.87 out of 5 average rating, 15 reviews

A spacious room features vaulted peak ceilings and two Queen beds with stylish wooden frames. A modern electric fireplace is positioned against the wall. Natural light fills the space, highlighting the warm wooden tones and cozy seating area with a circular rug.

Hotel room in Oakland

Cove Creek Lodge 204: Poolside Double Queen

The image displays a cozy room featuring a full bed with simple bedding. Exposed brick walls and large windows enhance the inviting atmosphere. The bathroom area is compact, showcasing a toilet and sink. A charming brick building exterior is illuminated, highlighting its historic architecture.

Hotel room in Meyersdale

4.66 out of 5 average rating, 129 reviews

Edison Room - GAP Trail Hotel at Morguen Toole Co

Hotel room in Berkeley Springs

A cozy bedroom is highlighted by a spacious bed covered with a patterned blanket, featuring a mountain and wildlife design. A quilted wall hanging adds a rustic touch. Two bedside lamps provide soft lighting, and a wooden table at the foot of the bed complements the decor.

4.82 out of 5 average rating, 38 reviews

Amber Room - Bed n Brew in Berkeley Springs WV

4.67 out of 5 average rating, 3 reviews

The spacious room features a King bed with a wooden frame and modern bedding. A kitchenette is visible in the background, alongside a Smart TV. Two leather chairs are situated near the bed, complemented by wooden flooring and soft overhead lighting.

Hotel room in Oakland

Cove Creek Lodge 219: Lakeside Executive King

Hotel room in Berkeley Springs

A cozy queen bed is adorned with a warm patterned comforter and a decorative bolster pillow. A textured gray pillow rests at the head of the bed. A bedside lamp features a textured base, adding a subtle detail to the room's decor.

4.78 out of 5 average rating, 46 reviews

Berkeley Room - Bed n Brew in Berkeley Springs WV

Hotel room in Capon Bridge

A bright bedroom features a spacious bed dressed in white linens, complemented by colorful accent pillows. A cozy reading chair is positioned beside a wooden dresser. Natural light filters through the nearby window, illuminating the room's soft blue walls and decorative wall mirror.

4.98 out of 5 average rating, 168 reviews

Sycamore Suite ~ 1 of 5 Unique Stays at Basswood

4.88 out of 5 average rating, 8 reviews

A spacious sleeping area features a large bed with crisp linens and soft pillows. Two bedside lamps provide warm lighting. A seating area includes a plush armchair and a wooden side table. Natural light enters through a large window next to a wooden wall.

Hotel room in Oakland

Cove Creek Lodge 206: Standard King Room

Hotel room in Capon Bridge

A bright and inviting bedroom features a queen bed with crisp white linens and a cozy armchair beside a small side table. A flat-screen TV is mounted above an elegant white fireplace, while windows with blinds allow natural light to fill the space.

4.98 out of 5 average rating, 96 reviews

Redbud Suite ~ 1 of 5 Unique Stays at Basswood

Other great vacation rentals in Cumberland

4.94 out of 5 average rating, 18 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

4.95 out of 5 average rating, 61 reviews

A cozy living area is showcased, featuring a plaid armchair beside a decorative bookshelf. The fireplace is framed by white bricks, complementing the rustic wooden accent wall. Art pieces adorn the space, while a bowl of vibrant flowers adds a touch of color to the setting.

Farm stay in Ellerslie

Historic Eden Ranch, built 1837

4.93 out of 5 average rating, 14 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

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.

4.9 out of 5 average rating, 58 reviews

Cozy Cottage

4.91 out of 5 average rating, 43 reviews

Home in Oldtown

Oldtown Guesthouse

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.

4.95 out of 5 average rating, 85 reviews

The Dacha. Rebirth sauna experience

The front view of the house features a welcoming porch with wooden decking, adorned with hanging flower baskets. An American flag is prominently displayed, complementing the light-colored siding and sloped roof under a partly cloudy sky.

4.94 out of 5 average rating, 33 reviews

Saratoga Stays! Close to C&O!