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.

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.

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.

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.

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.

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 !

The GreyLoo

Cozy, clean and friendly downstairs apartment. Stocked with all the things you need for a short stay as well as the long haul. Close to the Great Allegheny Passage, Main Street Frostburg, Frostburg State University, the Frostburg Pool, and many other locations. Located 33 mi from Wisp Resort/Deep Creek Lake and 18 mi from Rocky Gap Casino Resort. Just a few miles from I68. Enjoy this cozy place and bring your furry friends. Lots of nearby hiking, biking, and outdoor adventures.

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.

Chalet in the Orchard; Romance, Luxury, Relaxation

The Chalet in the Orchard was designed with Romance, Luxury, and Relaxation in Mind. The Chalet offers many first class amenties to Enjoy with your Partner. * Movie Theater with Surround Sound * Tonal Digital Home Gym * Dedicated Work Space * Fast Wifi * Sauna * Hot tub * Outdoor TV * Gas and Wood Burning Fire Pit * Private outdoor Seating * Large Soaking Bathtub * Luxury Stone tile Shower * Heated Tile Bathroom Floors * Full Kitchen * Breville Espresso Machine * King Bed

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.