House vacation rentals in Cumberland

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.

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.

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

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.

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).

The Woodland Getaway

The beautiful Woodland Getaway is tucked away from everyday hustle and bustle. Stretch out on a lounge chair & watch the wildlife on the elevated screened in porch surrounded on three sides by trees. Sit on the ground level back deck at dusk & wait for the deer to arrive. Secluded and private the Woodland Getaway is the perfect spot for rest and relaxation. Come enjoy the view of wildlife and sunsets through our beautiful bay windows and enjoy the quietness and serenity of mother nature.

The Dacha. Rebirth sauna experience

After a year of a complete renovation of the house, we invite you to visit a 122-year-old house that fully meets modern housing standards. We installed an advanced smart home system that controls lights, blinds, heating, and air conditioning and even helps you rate your sleep quality and listen your favorite music. For your culinary masterpieces, there is a full kitchen with all the necessary equipment and a basic set of spices. Please, absolutely No smoking on the property, and No pets

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.

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.

Allegany Retreat

This 1800s Duplex home has tons of charm & comfort! Close to Main street charm n shops and all that it offers. Original wood floors. Snacks & coffee for your enjoyment. Close to GAP trail n fantastic scenic views. Please NO LOUD noises after 10pm. ABSOLUTELY NO SMOKING inside our home in consideration of future guests We love animals but unfortunately they are not generally allowed. Exterior cameras for everyones security, front and back.

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

Abby's Lookout is conveniently located just outside historic Berkeley Springs, WV. You'll find solitude and everything else you'll need to enjoy a piece of West Virginia. The renovated space offers a large kitchen for cooking meals for your friends or family. Relax on the deck or in the elevated hot tub while soaking up the incredible starry views. Sleep well in either a queen size bed or two twins.

Piney Mtn House - Cozy 2BR Stay near Frostburg

Tucked into the mountains just outside Frostburg, this stylish renovated bungalow offers a quiet, cozy place to unwind. Enjoy a private yard, covered porch, and patio with fireplace—perfect for slow mornings and relaxed evenings. Thoughtfully designed for comfort, it’s an easy home base for exploring, hiking, visiting, or simply settling in.