Holiday rentals in Short Gap

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Top-rated holiday rentals in Short Gap

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite

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.

Home 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.

4.94 out of 5 average rating, 169 reviews

Top guest favourite

Home in Cumberland

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.

4.99 out of 5 average rating, 161 reviews

Guest favourite

Home in Corriganville

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.

4.91 out of 5 average rating, 108 reviews

Top guest favourite

A cozy bedroom features a spacious bed with decorative pillows, complemented by a unique wood-paneled accent wall. A desk sits nearby, illuminated by natural light from a large window that offers a view of the surrounding greenery, enhancing the room's serene atmosphere.

Cabin in Springfield

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.

5.0 out of 5 average rating, 111 reviews

Top guest favourite

The exterior of a renovated log cabin is showcased, featuring traditional log and chink construction. A substantial stone chimney rises alongside the cabin. A spacious porch is present, equipped with a couple of white chairs, surrounded by natural greenery and autumnal foliage.

Cabin in Springfield

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 !

5.0 out of 5 average rating, 165 reviews

Top guest favourite

A charming cabin stands amidst lush greenery, showcased by tall trees that frame its entrance. The front porch is accessible via a small set of stairs, with a path lined by gravel leading to the door. Natural light filters gently through the surrounding foliage.

Cabin in Frostburg

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.

4.95 out of 5 average rating, 118 reviews

Top guest favourite

The cottage is nestled among vibrant autumn foliage along the riverfront. A rock cliff rises behind it, while a winding path leads to the house, which is surrounded by a mix of colorful trees. The serene river can be seen nearby.

Cottage in Green Spring

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.

4.98 out of 5 average rating, 127 reviews

Top guest favourite

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.

Home in Cumberland

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.

4.92 out of 5 average rating, 160 reviews

Guest favourite

A side view of the home reveals a light blue exterior with large windows, surrounded by a lush green lawn. A wooden picnic table is situated on the grass, offering a space to enjoy the outdoors under the shade of a nearby tree.

Guest house in Cumberland

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.

4.92 out of 5 average rating, 103 reviews

Top guest favourite

A cozy living room is presented with a leather sofa and a rustic coffee table. A traditional bookshelf filled with decor and framed photos is situated against a brick wall. A television is mounted above a brick fireplace, enhancing the gathering space.

Townhouse in Cumberland

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.

4.94 out of 5 average rating, 287 reviews

Guest favourite

The entrance features a burgundy door framed by white trim. A small round table with two black wrought iron chairs is positioned beside the door. A potted plant is placed near the entrance, adding a touch of greenery to the inviting outdoor space.

Home in Frostburg

Allegany Retreat

This 1800s Duplex home has tons of charm & comfort! Close to Main street 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.

4.83 out of 5 average rating, 228 reviews

Top guest favourite

A spacious living area features a modern sofa and a comfortable lounge chair, complemented by a coffee table. A dining table with four chairs is positioned near a window, while greenery adds a touch of nature. Soft light filters through the windows, enhancing the serene atmosphere.

Flat in Cumberland

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.

4.99 out of 5 average rating, 101 reviews