House holiday 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, 273 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.

4.99 out of 5 average rating, 158 reviews

The ranch house is highlighted by a vibrant red roof, set against a backdrop of lush greenery. Large windows provide ample natural light, and a spacious patio with seating areas invites relaxation. The surrounding lawn is well-manicured, enhancing the property’s peaceful setting.

Home in Hyndman

Wills Mountain Ranch

Lovely, private home overlooking our beautiful valley with breathtaking views of Wills Mountain. It is the perfect setting for a family retreat/reunion. The ranch house has a red roof in the pictures. My husband & I live in the 3 story. We have a in-ground pool on property (heated from Mid-May to early September), a gas grill, and fire pit on the large scenic patio for your enjoyment. The large windows & patio offer a spectacular view of Wills Mt. The ranch house offers a quiet getaway retreat.

5 out of 5 average rating, 126 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.

4.92 out of 5 average rating, 316 reviews

An aerial view captures the cottage nestled among vibrant autumn foliage, surrounded by colorful trees. The serene pond reflects the rich hues of fall, while solar panels are visible on the cottage roof. A winding dirt road leads to the property, enhancing the secluded atmosphere.

Home in Clearville

Grouseland's Pondside Vacation Cottage

Set about a quarter mile of the road, our pet friendly solar powered vacation cottage is a perfect getaway for anyone trying to spend some alone time with nature! Guests have complete privacy inside the cottage with a full kitchen, two TV's, Wi-Fi, and a mini split system for heating and cooling. As well as exclusive access to the hot tub, fire pit and pond outside! We also have various shared hiking trails through the woods surrounding the cottage for campers and cottage guests to enjoy!

The exterior entryway features a set of stairs leading to a porch with white railing and overhead lighting. A small bush is visible beside the stairs, and the brick façade of the home provides a warm appearance, enhanced by the nighttime ambiance.

4.94 out of 5 average rating, 105 reviews

Great Location, Spacious, Comfy 2 bdrm 3 bed home

This home is centrally located near all things fun and exciting to do in Cumberland. Situated in a quiet residential neighborhood in the Western Maryland mountains. Minutes from historic downtown, the Potomac River, Rocky Gap State Park, Pennsylvania, the University of Pittsburg Medical Center, the C &O canal and much more. This home features 3 queen beds, 2 bedrooms both with 55" TV's and blackout curtains, a large separate dining room, a spacious kitchen, and living room with a 65" TV.

4.94 out of 5 average rating, 233 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.

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, 167 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, 565 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, 137 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, 325 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, 144 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.

4.99 out of 5 average rating, 108 reviews

The kitchen showcases white cabinets contrasted by sage green lower cabinets. Modern appliances, including a dishwasher and gas stove, are present. A farmhouse-style dining area with a small table and two chairs is nestled by a window, illuminated by natural light.

Home in Frostburg

Piney Mtn House

Become part of Mountain Maryland discovering your next cozy escape in the newly renovated modern bungalow. The Appalachian range will tuck you in the small town of Eckhart, closely boarding Frostburg, with all its unique attractions, entertainment, hiking trails, and state parks. No body does small town like local Frostburg. And there is no better way to unwind than to make the Piney Mountain House your home away from home.

Popular amenities for house rentals in Cumberland

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

The exterior of the bungalow features a large deck with multiple seating areas and a screened-in porch beneath a sloped, blue gabled roof. Surrounding trees showcase autumn foliage, and a staircase leads from the deck to the ground, where fallen leaves blanket the yard.

4.97 out of 5 average rating, 39 reviews

'Little Blue Bungalow' in The Woods-pool access

The cabin features a green exterior with a distinctive gabled roof and wooden accents. Two yellow chairs are placed on a small wooden deck at the entrance, surrounded by lush greenery and gravel pathways, enhancing the natural woodland setting.

4.84 out of 5 average rating, 43 reviews

Cabin w/King Bed, Hot Tub

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.

5 out of 5 average rating, 106 reviews

Spacious & Charming! Large deck+Game shed+Firepit

4.88 out of 5 average rating, 59 reviews

Dog-Friendly A-Frame w/Firepit & Near Trails

A spacious living area is shown, featuring two sofas and an armchair arranged around a circular coffee table. Large windows allow natural light to fill the room, while a stone fireplace adds a rustic touch. The adjacent dining area is visible in the background.

4.96 out of 5 average rating, 67 reviews

Spacious Lodge Perfect for Year Round Getaway

A spacious living area is furnished with teal sofas and a decorative rug. Large windows allow natural light to fill the room, revealing views of the outdoors. A contemporary coffee table and stylish decor complement the overall design, with a ceiling fan maintaining a comfortable atmosphere.

5 out of 5 average rating, 35 reviews

Magic Mountain Retreat - Mountain View, EV charger

An open living area features a comfortable gray sofa and a round wooden coffee table on a textured area rug. The kitchen showcases modern appliances and barstool seating at the island, with natural light filtering through windows that highlight the neutral tones and rustic ceiling beams.

4.95 out of 5 average rating, 21 reviews

The Stairway to Heaven

4.89 out of 5 average rating, 65 reviews

The exterior of the home displays a charming log cabin design with a stone foundation, surrounded by trees. A covered front porch features a railing, while two chairs are positioned for relaxation. A gravel driveway leads to the entrance below, maintaining a blend of natural elements.

Home in Swanton

Updated Baths, Wood Fireplace, Hot Tub & Fire Pit

Weekly house rentals

5 out of 5 average rating, 33 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

A scenic view of rolling hills under a pastel sky at sunset, with a fence line in the foreground. A hot tub is situated on a spacious deck, surrounded by scenic greenery. A cozy living area features a neutral color palette, a comfortable seating arrangement, and soft lighting. The exterior showcases a charming house on expansive grounds.

4.98 out of 5 average rating, 349 reviews

Abby's Lookout - Raised Retreat w/Hot Tub & WiFi

4.75 out of 5 average rating, 4 reviews

Home in Ridgeley

The Western Maryland Retreat

A staircase with wooden steps leads to the upper level, flanked by exposed brick walls and dark blue accents. A shelf displaying decorative items complements a dining table, while a potted plant adds a touch of greenery. Natural light fills the open space, enhancing its inviting design.

4.93 out of 5 average rating, 43 reviews

Paloma House Retreat

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.

4.73 out of 5 average rating, 67 reviews

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

A small, inviting house is situated on a corner lot surrounded by greenery. The exterior features a metal roof and a front porch with two chairs, and steps lead up to the entrance. Nearby trees provide a natural backdrop.

4.99 out of 5 average rating, 90 reviews

Small, cheerful house!

4.87 out of 5 average rating, 690 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

A modern kitchen is displayed, featuring light gray cabinets and stainless steel appliances. A patterned rug lies on the tiled floor, enhancing the space. Natural light enters from the windows above the sink, illuminating the organized countertops with various kitchen items.

4.88 out of 5 average rating, 25 reviews

Mountain Maryland Getaway

Private house rentals

A three-story house features a welcoming entrance with red steps leading up to a door framed by large windows. The exterior is a combination of beige siding and stone, and a Maryland state flag is displayed prominently. A grassy lawn surrounds the house.

5 out of 5 average rating, 35 reviews

Spacious Parkside Oasis!

4.95 out of 5 average rating, 22 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

The A-frame lodge features a distinctive shape with a steeply pitched roof and large front windows. A welcoming green door is framed by wooden steps, leading to a spacious deck. Surrounding greenery offers a peaceful, natural setting.

4.94 out of 5 average rating, 84 reviews

Berkeley Springs Jungle Lodge

5 out of 5 average rating, 15 reviews

A wooden sign displays 'The Farmhouse at Poverty Knob,' suspended from a decorative black metal post. The sign is positioned in a lush green landscape, with trees and rolling hills visible in the background.

Home in Green Spring

The Farmhouse at Poverty Knob

4.91 out of 5 average rating, 46 reviews

Home in Oldtown

Oldtown Guesthouse

5 out of 5 average rating, 14 reviews

The iconic 1907 home is surrounded by lush green lawns, featuring a detailed façade with multiple balconies and large stone columns. The hillside backdrop enhances the property’s historic charm, with a clear blue sky and fluffy clouds above.

Home in La Vale

Mountain view Grand 6BR in LaVale |15min Rocky Gap

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.

4.92 out of 5 average rating, 39 reviews

Saratoga Stays! Close to C&O!

A covered porch with wooden beams offers a welcoming seating area featuring white chairs and a multi-colored swing. Lush greenery and flower beds enhance the outdoor space, which is framed by well-maintained grass and a paved driveway.