House holiday rentals in Cumberland

4.93 out of 5 average rating, 149 reviews

Rails and Trails Retreat ~ historic home w. yard

Spacious, beautifully restored historic home in a prime Cumberland location perfect for families, couples, and groups exploring Western Maryland. Just 100 feet from the GAP and C&O Canal trails, and an easy walk to downtown historic Cumberland with restaurants, cafés, shops, and the train station. The home blends historic charm with modern comfort, offering generous living space across three levels, a fully equipped kitchen, and a large private backyard - a peaceful retreat after a full day out.

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, 276 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, 147 reviews

A single-story blue house is set against a backdrop of leafy trees. The front porch features a welcoming red door and two outdoor chairs. Soft landscaping surrounds the house, which has a neatly maintained lawn and a paved driveway leading to the entrance.

Home in Romney

Southern Charm Getaway in Romney, WV - Sleeps 6

Beautiful, comfortable & clean family friendly getaway in West Virginia's first town! Located in the center of town and walking distance to restaurants, public library, boutiques, shopping, historical sites, Civil War trenches, public pool and Visitor's Center. Just a few short miles to The Potomac Eagle Scenic Excursion Train & to the South Branch of the Potomac River for fishing and canoeing. You will find many day trip activities within an hours' distance, including Skiing, hiking &biking

5 out of 5 average rating, 129 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, 319 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, 107 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, 235 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.

4.85 out of 5 average rating, 169 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.

4.87 out of 5 average rating, 330 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.

4.98 out of 5 average rating, 147 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.

4.89 out of 5 average rating, 103 reviews

An outdoor fire pit area is surrounded by gravel and features three wooden Adirondack chairs arranged around a stone fire ring. Softly glowing string lights are draped between tall trees, creating a cozy ambience amidst the forest setting.

Home in Accident

Peaceful nature retreat nestled in a forested area

Welcome to our lovely vacation House! Built in 2024, fresh, cozy and modern. Perfect for memorable family trip, romantic getaway for a couple or a fun adventure for a small group of friends. Convenient location- great combination of privacy (forest-like area) and quick access to fun places: 5-10 minutes drive from Wisp Ski Resort, Deep Creek lake, boat rentals, scenic hikes, restaurants, bars, amusement parks and grocery stores.

4.98 out of 5 average rating, 114 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

4.98 out of 5 average rating, 42 reviews

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.

Home in Hedgesville

'Little Blue Bungalow' in The Woods-pool access

5 out of 5 average rating, 111 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

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, 37 reviews

Magic Mountain Retreat - Mountain View, EV charger

A spacious bedroom features a large bed covered with a neutral-toned blanket. A cozy seating area with a patterned chair and lamp is visible near a window. A dresser and a shelf line the wall, contributing to the room's functional layout.

4.82 out of 5 average rating, 44 reviews

Mayapple

5 out of 5 average rating, 54 reviews

Home in Clearville

5 -Star Luxury Mountain Getaway - Grandview Lodge

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.

4.93 out of 5 average rating, 92 reviews

The Dacha. Rebirth sauna experience

The chalet is surrounded by towering trees, showcasing a seasonal display of vibrant autumn foliage. A screened-in porch extends from the structure, providing a shaded space. The home integrates seamlessly into the natural landscape of the Appalachian Mountains, creating a tranquil and inviting retreat.

4.84 out of 5 average rating, 76 reviews

Autumn Wings - wifi, screen porch, pool access

4.9 out of 5 average rating, 101 reviews

The exterior of the Craftsman-style home features a welcoming front porch with wooden rocking chairs. Lush green shrubs and blooming flowers add color to the landscape, while a spacious deck is visible in the background. A stone path leads to the front entrance.

Home in Oakland

Spacious Home Near All Deep Creek MD Has to Offer

Weekly house rentals

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, 354 reviews

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

4.89 out of 5 average rating, 163 reviews

The exterior of a vintage red schoolhouse is shown, featuring white picket fencing and a gravel driveway. A flagpole stands proudly with the American flag, while the surrounding landscape includes gently rolling hills. Soft lighting from the house illuminates the entryway, enhancing the inviting appearance.

Home in Cross Junction

Little Red Schoolhouse in Cross Junction

A view of the house is framed by lush greenery, showcasing a brick exterior with a dark roof. The surrounding trees create a sense of privacy, while a driveway leads up to the entrance, inviting guests to explore the space.

4.99 out of 5 average rating, 186 reviews

Lomalinda quiet retreat + walk to Berkeley Springs

4.94 out of 5 average rating, 109 reviews

An A-Frame home is surrounded by trees, featuring a stone patio with four black lounge chairs arranged around a circular fire pit. The exterior is fitted with large windows, allowing for ample natural light.

Home in Gerrardstown

A-Frame Mountain 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.

4.94 out of 5 average rating, 47 reviews

Paloma House Retreat

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.

4.73 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, 95 reviews

Small, cheerful house!

4.87 out of 5 average rating, 697 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

Private house rentals

5 out of 5 average rating, 37 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

4.96 out of 5 average rating, 26 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

4.86 out of 5 average rating, 7 reviews

Home in Ridgeley

The Western Maryland Retreat

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.

4.93 out of 5 average rating, 95 reviews

Berkeley Springs Jungle Lodge

4.91 out of 5 average rating, 23 reviews

A modern cabin is nestled on a grassy hillside, framed by trees and open farmland. The structure is accented with warm lighting from windows and features a private hot tub on a stone patio. A fire pit with seating is visible, enhancing the outdoor setting.

Home in Augusta

Sun Valley Overlook A-Frame | Wow Views + Hot Tub

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, 62 reviews

Cozy Cottage

5 out of 5 average rating, 16 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