Pet-friendly holiday 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.

Walkability · Pets · TV

Mountain View Acres Getaway

Enjoy nature in a beautiful peaceful setting with 100 acres of privately owned property. Breathtaking panoramic views spanning 45 miles in a tranquil natural spot with hiking trails throughout. Handicap accessible. Within a short drive of 2 major ski resorts, the Flight 93 Memorial and 2 wineries. Several restaurants and a brewery also within a 15 minute drive. The property includes an outside firepit that is a favorite place for guests to relax and enjoy the breathtaking views of the mountains.

Pets · Walkability · Access

Covered Deck, Fire Pit, Hot Tub, Outdoor Shower

Escape to our modern industrial-chic-ish cabin nestled in the woods. A wilderness haven where contemporary and creative design meets nature face-to-face. Disconnect from the modern world, find inspiration, and create lasting memories. Embrace rustic elements, sleek lines, and raw textures. Renew creativity, bond with friends and loved ones, and embark on thrilling adventures while immersing yourself in the serenity of nature's embrace. Milam Ridge offers all of these experiences and more.

Outdoor spaces · Pets · Location

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).

Pets · Outdoor spaces · Check-in

Mountain Oasis Cottage

Our Cottage is located at the base of a mountain on a dead end road it is very tranquil with a lot of deer that feed in the back yard. We are 15 minutes from the city of Cumberland Maryland where the “Western Maryland Bike Trail” is located and 30 minutes from historic Bedford, PA. The Cottage has two bedrooms that each feature queen size beds, one living room with a pull out queen size sofa bed, and a sitting room with a full size pull out sofa bed. Heated and cooled w/ mini splits.

Outdoor spaces · Pets · Checkout

Martha’s Cabin

Mountain Maryland's private cabin retreat is a completely renovated 1 bedroom, 1 bathroom getaway perfect for up to two guests. The peaceful wooded surroundings with walking paths to the property's creek will bring you relaxation and peace. Only minutes from Frostburg's small town attractions, Frostburg State University campus, downtown entertainment, shopping, local area hiking trails and state parks! Martha's Cabin is a perfectly tucked away yet with everything you need nearby.

Walkability · Pets · Parks

Easygoing

Tired of the chaos and need a place to unwind and relax ? We have the perfect place for you! A quaint, quiet cabin to let you clear your mind and spirit after a day of hiking, biking or kayaking since we are only five miles from both the Paw Paw tunnel and the Potomac river. The cabin is equipped with electric, heating, stove top, microwave, large deck, hammock chairs, horseshoe pit, 2 double size futons with room to spare, indoor toilet but BEST of all is showering outside!

Pets · Outdoor spaces · Comfort

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.

Outdoor spaces · Pets · View

The River House

A cozy, spacious and private get away with access to entire finished house. Located river front of the South Branch of the Potomac River, giving it the best view in the area. This cottage is also within 3 miles of C&O Canal, 17 miles from Historical Romney, 15 miles to Cumberland, MD and 10 miles to the Paw Paw, WV tunnel. 2 kayaks and 1 canoe available for river excursions. Come enjoy hiking, biking, kayaking, fishing or simply soak in all nature has to offer in the backyard.

Pets · Outdoor spaces · Family

The Shadoe on Greene

Just a stones-throw from everything Cumberland has to offer, The Shadoe on Greene is at the heart of it all. Literal steps from the Western Maryland Scenic Railroad, the Great Allegheny Passage trail & the Historic City Center, with a wide array of local shops and eateries. This unique property was built in the 1850's and has been lovingly restored to embrace it's history, as well as provide all of the modern amenities you'd expect.

Pets · Outdoor spaces · Heating

Sweet 68

This stylish and unique place sets the stage for a memorable trip. You will feel right at home in this studio equipped with all the conveniences of home. Studio is in own private space with own entrance where you can sip some coffee on either of the patios. It is also located steps away from the hot tub. This studio apartment is located 1 mile off interstate 68. It is convenient to local restaurants in walking distance.

Pets · Outdoor spaces · View

Hummingbird Ridge

Amazing views! This cozy cabin overlooks the Potomac Valley and Greenridge state forest. Enjoy viewing mountains ranges from 3 states. Unbeatable star gazing. Berkeley Springs is 13 miles away. The Paw Paw tunnel is 9 miles away. Plenty of local hiking, kayaking and fishing. The perfect getaway for a nature loving small family. We looking forward to having you on the mountain!

Walkability · Pets · Long stay