Vacation rentals in Short Gap

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.

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.

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.

Steeple View Flat in Historic District

Relax in your first level flat. Entire private efficiency suite with a secure self check in. The entrance located along side of the main house in Cumberland’s Historic District. You can safely park your car and walk to many of Cumberlands amenities. If you’re biking, they can be stored inside. Canal Place has unique shops a winery and a bike rental facility. Cumberland theater is adjacent to the property, also Baltimore St. Promenade offers a delicious choice of indoor and outdoor dining.

1832 Historic Washington Bottom Farm Log Cabin

Welcome to our renovated 1832 Log Cabin on the grounds of the George William Washington and Sarah Wright Washington 19th century plantation. The cabin was the first structure built. Then came barns and slaves’ quarters (no longer standing). The dairy barn is now a woodworking shop and the bank barn was recently restored. The main house, built in 1835, is Greek Revival style. Today, our 300+acre is Certified Organic. We border the South Branch of the Potomac River. It’s ALMOST HEAVEN !

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.

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.

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.

The Hidden Tree

Nestled in the heart of Cumberland. Our cozy home offers a perfect blend of comfort and convenience for your stay. Whether you're here for business or leisure, we've got you covered! Conveniently located near UPMC Hospital, Planet fitness, Downtown Cumberland, Rocky Gap Casino and much more! Explore the vibrant neighborhood or venture out to discover the hidden gems of Cumberland. Book your stay at “The Hidden Tree” today and make unforgettable memories.

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.

Corner Tavern-Allegheny Suite

Nestled above Corner Tavern & Cafe in historic downtown, this newly renovated modern apartment supplies you with all the comforts of home in a tasteful design. Our location provides all the benefits of a night out of town, located in historic downtown, above a tavern & cafe, you'll find food, drink & maybe even music in a few short steps from your apartment.

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.