House holiday rentals in Cumberland

A historic home is framed by lush greenery and vibrant red trees. The front features a welcoming porch with ample steps leading up to the entrance, while architectural details highlight the charm of the period. Windows add character to the inviting façade.

4.94 out of 5 average rating, 155 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.

4.92 out of 5 average rating, 279 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, 159 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.

4.99 out of 5 average rating, 140 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.

4.95 out of 5 average rating, 166 reviews

The cabin is illuminated at night, showcasing its rustic charm among surrounding trees. Warm lights accentuate the porch and pathway, enhancing the inviting atmosphere. The outdoor space is highlighted by well-placed rocks and greenery, creating a serene outdoor retreat.

Home in High View

Mtn. View~Cave Hot Tub~50 Ac~ATV Trails~Fish~Swim

Mountain home: like in the movies, on 50 acres. Includes soaring mountain views, swimming holes, hiking trails, ATV trails, fishing creek, mini white sand beach, hot tub in a cave, huge boulder rustic fire pits, cave, lake, cabanas, all in a heavy forest exclusively for guests. Private: you cannot see another house from the front porch or back decks and it has thick woods all around. At the top of the property are soaring views with 3 miles of visibility. No need to go to the national park.

4.93 out of 5 average rating, 332 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 off 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!

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, 583 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, 141 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.

4.99 out of 5 average rating, 151 reviews

A modern kitchen and dining area feature sleek white cabinets and a butcher block countertop. A central island with stools provides additional seating. The space is well-lit through large windows, with a dining table positioned nearby and a living area visible in the background.

Home in Fort Hill

KLAE House - nestled among the trees

The KLAE House is perfectly situated within sight of the GAP Bike Trail and within walking distance to the Casselman River. Also, centrally located near Ohiopyle State Park, Seven Springs Mountain Resort, Yough Lake, Frank Lloyd Wright homes, and much more. This home has been completely renovated and designed with a unique vintage/modern style. The KLAE House is the perfect getaway for a quiet and peaceful stay surrounded by nature on your own private hillside.

4.98 out of 5 average rating, 150 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.

4.98 out of 5 average rating, 120 reviews

A patio area is featured with two chairs and a small table atop a concrete surface. Lush green grass surrounds the space, while vibrant yellow daffodils bloom in the foreground, adding a touch of color to the natural setting. A stone fireplace is visible in the background.

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.

4.91 out of 5 average rating, 144 reviews

The modern cabin is set on a serene hillside, featuring a spacious deck with a hot tub and fire pit. Large glass windows offer mountain views, while the soft evening light casts a warm glow over the outdoor space, surrounded by lush greenery.

Home in Augusta

Hart's Overlook | HOT TUB, Mtn Views + Pond!

BNB Breeze Presents: Hart's Overlook! Experience the West Virginia Mountains from our newly-built retreat! With a private hot tub, fire pit, and picturesque views of the West Virginia Mountains that you get with your personal retreat in paradise! This newly built modern cabin includes: - HOT TUB! - Fire Pit - Smart TV - Charcoal Grill - Hilltop Pavillion - Private Pond! - Picturesque Views

Popular amenities for Cumberland house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Superhost

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, 57 reviews

Cabin w/King Bed, Hot Tub

4.88 out of 5 average rating, 67 reviews

Home in Hedgesville

Dog-Friendly A-Frame with Hot Tub and Firepit

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, 75 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, 38 reviews

Magic Mountain Retreat - Mountain View, EV charger

4.95 out of 5 average rating, 237 reviews

The lodge features a striking architectural design with a wooden ceiling and stone accents, surrounded by a forest backdrop. A large deck with wooden railings extends from the structure, providing a welcoming entrance to the space.

Home in Oakland

Hot Tub By Fireplace+Firewood/Pool Memb.-Lge Deck

4.93 out of 5 average rating, 44 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

4.9 out of 5 average rating, 69 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

4.96 out of 5 average rating, 52 reviews

The entrance to the guest house is showcased, featuring a combination of brick and stone siding. A welcoming red door is flanked by large windows, and a decorative wreath adds a touch of charm. The pathway is lined with neatly trimmed shrubs and grass.

Home in Big Pool

Whitetail Meadows Guest House

Weekly house rentals

4.97 out of 5 average rating, 29 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

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, 54 reviews

Paloma House Retreat

A modern kitchen with a white countertop showcases a simple bowl of greenery. A dining table with four wooden chairs is visible, while soft natural light fills the open living area, featuring cozy seating and a stone fireplace. The space is accented by exposed wooden beams.

4.91 out of 5 average rating, 127 reviews

Simply Scandi- Modern Mt Retreat

5 out of 5 average rating, 26 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

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, 37 reviews

Mountain Maryland Getaway

4.91 out of 5 average rating, 333 reviews

A panoramic view of lush green mountains stretches out below, with a soft sunrise illuminating the horizon. The scene captures varying shades of green from the trees, contrasting with the delicate pastel colors of the sky.

Home in Hedgesville

Round Mountn Top House! Prof. Cleaned w EV-chrger

4.81 out of 5 average rating, 117 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

5 out of 5 average rating, 19 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

Private house rentals

4.94 out of 5 average rating, 49 reviews

A welcoming porch is adorned with a seasonal wreath on the entrance door. The word 'FARM HOUSE' is prominently displayed on the white wall, complemented by two rocking chairs and a red cushioned chair arranged for relaxation. Soft sunlight illuminates the space.

Home in Frostburg

Farm House 1875

4.97 out of 5 average rating, 72 reviews

The charming black structure is set against a backdrop of lush green trees and a tranquil river at sunset. Reflections of the house and trees shimmer on the calm water, creating a serene outdoor atmosphere.

Home in Grantsville

Riverside Cabin! Riverfront Sauna! Theater Room!

5 out of 5 average rating, 43 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

4.85 out of 5 average rating, 13 reviews

Home in Ridgeley

The Western Maryland 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

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

4.92 out of 5 average rating, 52 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 bulldog rests comfortably on a wooden porch. The dog is wearing a tactical vest featuring a bear patch. The legs are positioned at an angle, showcasing the relaxed posture. The colorful backdrop of the house can be seen, enhancing the serene setting.