House 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, 275 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, 146 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, 127 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, 106 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.

A stone fireplace rises from the floor to the ceiling, flanked by two large windows adorned with sheer curtains. A simple wooden coffee table rests on a light-colored area rug, while a flat-screen TV is positioned nearby on a wooden stand, creating a cozy living space.

4.98 out of 5 average rating, 119 reviews

Our Shangri La

Take it easy at this unique and tranquil getaway. Our Shangri La is located above Prospect Overlook. National Geographic Magazine rated Prospect Overlook as one of the five best in the East. Views include three states: Pennsylvania, Maryland and West Virginia; and two rivers, the Potomac and Cacapon. Our Shangri La is 3 miles from the town of quaint town of Berkeley Springs, 9 miles from the picturesque Cacapon State Park and Cacapon Resort and golf (Robert Trent Jones masterpiece).

4.94 out of 5 average rating, 234 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, 572 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, 140 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.

4.98 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, 101 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.

Popular amenities for Cumberland house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.95 out of 5 average rating, 42 reviews

A charming house with a multi-gabled roof and large front porch is surrounded by well-maintained landscaping. Green shutters complement the neutral siding, while stone accents add texture. Lush green grass and flowering shrubs enhance the exterior appeal, with a clear blue sky overhead.

Home in McHenry

Large 5 BR - Steps from Lake & Wisp!

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.

4.86 out of 5 average rating, 51 reviews

Cabin w/King Bed, Hot Tub

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, 71 reviews

Spacious Lodge Perfect for Year Round Getaway

5 out of 5 average rating, 27 reviews

The exterior of the rental home features a contemporary design with a gabled roof and wooden accents. A landscaped area with boulders and shrubs surrounds the front, while a spacious porch is supported by sturdy columns. Clear blue skies provide a bright backdrop.

Home in McHenry

Ski Home, Indoor Pool, Firepit, Hot Tub

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, 36 reviews

Magic Mountain Retreat - Mountain View, EV charger

4.89 out of 5 average rating, 28 reviews

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.

Home in Hedgesville

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

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

Weekly house rentals

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, 45 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, 94 reviews

Small, cheerful house!

4.92 out of 5 average rating, 48 reviews

A welcoming living area is shown, featuring a light rug and hardwood flooring. A comfortable sofa and armchair are positioned near a round ottoman. Natural light fills the space through the glass door and window. A modern shelf holds decorative items, and a wall clock adds functionality.

Home in Oldtown

Oldtown Guesthouse

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.

4.89 out of 5 average rating, 27 reviews

Mountain Maryland Getaway

A serene view of a river winding through a lush forest. A charming two-story building with a red roof is positioned near the water's edge, surrounded by greenery. The landscape features rocky banks and a variety of trees, creating a peaceful rural setting.

4.9 out of 5 average rating, 155 reviews

Peaceful Waterfall House is waiting for you.

4.83 out of 5 average rating, 108 reviews

A modern two-story home with a striking black and wood exterior is surrounded by lush greenery. The expansive deck extends from the main floor, providing outdoor space to enjoy nature. Large windows invite natural light into the interior, creating a bright and airy atmosphere.

Home in McHenry

Here on Holiday

4.93 out of 5 average rating, 108 reviews

A well-equipped kitchen features wooden cabinetry and an island with seating for four. Natural light fills the space, highlighting the polished wood floors. A full-size refrigerator, stove, and microwave are visible, along with counter appliances and a window offering an outdoor view.

Home in Markleton

The Country Ranch

Private house rentals

5 out of 5 average rating, 36 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 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, 36 reviews

Spacious Parkside Oasis!

4.86 out of 5 average rating, 7 reviews

Home in Ridgeley

The Western Maryland Retreat

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

5 out of 5 average rating, 16 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.

4.93 out of 5 average rating, 42 reviews

Saratoga Stays! Close to C&O!

5 out of 5 average rating, 16 reviews

The exterior view showcases a two-story blue house set on a grassy hillside, surrounded by tall trees. A covered porch with white railings offers shaded seating, and a staircase leads to the entrance. Lush greenery adds to the natural setting.

Home in Green Spring

The Rivers Edge