House holiday rentals in Cumberland

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, 101 reviews

Berkeley Springs Jungle Lodge

Welcome to the Berkeley Springs Jungle Lodge! Getaway from it all and stay at this stress free jungle themed lodge. Enjoy morning coffee on the back deck or sit under the stars while having a fire while overlooking your own private stream! Get the feeling of staying in the "jungle" while also being close to tons of activities, festivals, parks and other local attractions! The lodge is right off highway 522 and an 8 minute drive from Cacapon park, it is 12 minutes from downtown Berkeley Springs!

The historic brick home features a detailed façade with large windows framed by white columns. A wooden staircase leads to a welcoming porch, surrounded by snow-covered landscaping. Tall evergreen trees are visible in the background, creating a serene and inviting setting.

4.93 out of 5 average rating, 151 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, 277 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, 153 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, 130 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.

4.93 out of 5 average rating, 324 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!

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, 109 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, 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 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, 581 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.

4.86 out of 5 average rating, 332 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, 148 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.

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.

4.98 out of 5 average rating, 43 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.

4.87 out of 5 average rating, 52 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, 115 reviews

Spacious Retreat for Groups, Well Stocked

4.89 out of 5 average rating, 63 reviews

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

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

4.95 out of 5 average rating, 236 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 Firepl.+F.wood-Lge Back Deck-Pool memb.

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.

4.91 out of 5 average rating, 33 reviews

The Stairway to Heaven

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.

4.94 out of 5 average rating, 93 reviews

The Dacha. Rebirth sauna experience

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, 357 reviews

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

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

4.91 out of 5 average rating, 11 reviews

Home in Ridgeley

The Western Maryland Retreat

4.85 out of 5 average rating, 107 reviews

An ornate sign features an illustration of a vintage steam locomotive, with the words 'Pap's Place' prominently displayed below. The sign is mounted against a wooden background, creating a rustic appearance that highlights the home's connection to railroad themes.

Home in Rockwood

Pap's Place

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, 51 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

4.82 out of 5 average rating, 119 reviews

A bright living area is furnished with two comfortable sofas and a coffee table, positioned on a patterned rug. A wall-mounted television is displayed above a sleek console, complemented by natural light filtering through the large windows.

Home in Oakland

The Wise Quack - A Taste of Deep Creek Lake!

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.

4.92 out of 5 average rating, 120 reviews

Simply Scandi- Modern Mt Retreat

Private house rentals

5 out of 5 average rating, 41 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

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

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.

4.91 out of 5 average rating, 64 reviews

Cozy Cottage

4.92 out of 5 average rating, 51 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 presented with teal cabinetry and a farmhouse sink. Stainless steel appliances include a gas range and a dishwasher. Open shelving displays glassware, while the textured walls add depth. Natural light fills the space through the adjacent window.

5 out of 5 average rating, 18 reviews

The Cowbell

5 out of 5 average rating, 20 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

4.92 out of 5 average rating, 52 reviews

A spacious dining area is highlighted by a round table surrounded by wooden chairs, with a patterned rug beneath. A second table is visible, paired with chairs, and decorative elements on the walls create a cozy atmosphere. Natural wood finishes enhance the warmth of the space.

Home in Springfield

Camp Cliffside River Retreat