If you are looking for a place with scenic bike trails, refreshing mountain views, and rich history, then visit Cumberland. English colonizers established Fort Cumberland in the 1800s as a base during the French and Indian War. Cumberland Road and trains like the Western Maryland Railway were used to transport timber, coal, and iron ore mined from their mountains to supply the Industrial Revolution. The city also boomed as a manufacturing hub for glass, tinplate, breweries, and fabrics.
Cumberland declined economically after World War II, and most of its people migrated to nearby cities. However, the historical 19th to 20th-century buildings remained, and the scenic mountain countryside continues to attract tourists all year round. These Airbnb vacation rentals in Cumberland, Maryland, offer cozy, home-like stays with a classic vintage vibe. Select one from our list below!
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 06, 2024.
1. Bright 1 bedroom — great location
This private room is in a century-old house minutes away from Washington St., Cumberland Theater, Western Maryland Railway Station, Downtown Cumberland, GAP, I-68, and Amtrak Station. The spacious room has soothing pastel walls, carpeted flooring, and wide windows with city views. It has a cozy queen bed that sleeps two guests, air conditioning, and free WiFi. Guests may use the full bathroom across the hall with hot water and free toiletries. They may also use the kitchen to cook and eat simple meals, and the living room and bar area to relax or watch cable TV. Use of laundry equipment and long-term stays are allowed. Bikes are parked inside the garage while street parking is for cars.
Cumberland, Maryland, United States
11.33 km (7.1 mi) from Rocky Gap State ParkAccommodates: 2
Top guest reviews
Amenities & Room:
room was a bit sparse but comfortableour room was very comfortable with a private bath across the hallCleanliness:
very clean and stylish homenice clean and exactly as describedthe bedroom is simple but clean and comfortablehis house was clean and comfortablevery clean close and quietHost:
jake is a great hostjake is a great hostjake is a great hostjake was super kind and helpfuljake's a great host with fast respondRead more reviewsLocation:
awesome location walking distance from downtowngreat location in downtown cumberlandgreat location to downtownlocation is good toogreat location near all restaurants and areas of interest
2. Wesley's Playhouse
This massive property on Frostburg’s main street is two blocks away from restaurants and shops and half a mile away from the University and The Great Allegheny Passage rail trail. The huge house has a lush green garden at the back with a hammock and a gazebo. This two-story home accommodates 16 guests. The living room has sofas for warming up beside the fireplace or while listening to music played on the piano. The fully stocked kitchen is beside a huge dining area where you can enjoy family meals and free breakfast. The three spacious, fully air-conditioned bedrooms have a total of eight beds composed of a queen bed, full bed, two futons, two loft beds, and two foldaway bunk beds. The two full bathrooms have free toiletries and hot water. There are toys and sports equipment kids and adults can play with. Enjoy free WiFi, ethernet connection, central heating, laundry facilities, free parking, and free use of kayaks during summer.
Frostburg, Maryland, United States
24.39 km (15.2 mi) from Rocky Gap State ParkSuperhost
Accommodates: 16
Top guest reviews
Amenities & Room:
wifi is available and provides a good connectiongreat snacks and breakfast amenitiesthe breakfast included was great-- kids were not allowed to go to bed until completed -- yes i am that mean momkitchen has everything you need and breakfast was included has a nice outdoor space as wellCleanliness:
it was clean and the bed was comfortablecomfortable clean apartment and great communication made this another easy stayit’s cozy clean and convenientwesley’s playhouse is spacious clean and invitingit was extremely clean and the breakfast items were such a nice touchHost:
wesley was a great hostwesley was communicative and helpfulhosts responded promptly to any questions and were very helpfulwonderful place with great hostswesley was a great host and let us know about all the local spots to check outRead more reviewsLocation:
great location close to downtown frostburggreat place with convenient locationgreat in town locationgreat location and good valueit's so close all the main st attractions and the university
3. Braddock House (from USD 120)
This charming modern two-story home is in a quiet neighborhood near the highway and city center. It’s a few miles away from restaurants, shops, and Western Maryland Scenic Railroad. The second floor has three well-kept bedrooms featuring double beds that can sleep up to six guests, air-conditioning, free WiFi, and heating. The accommodation has one-and-a-half baths with free essentials. The ground floor has a living room with cozy sofas, flat-screen TV, and indoor fireplace. Guests can have family meals in the fully equipped kitchen and dining area. The house is surrounded by a lush green scenery with deer wandering around. It also has laundry facilities and free parking on the property.
Cumberland, Maryland, United States
13.08 km (8.2 mi) from Rocky Gap State ParkAccommodates: 6
Top guest reviews
Amenities & Room:
furniture and bedding are comfortablevery comfortable for two people and plenty of space to both relax and workthe beds are amazingly comfortable and ivone has thought about all the detailsthere are 3 bedrooms each with a full size bed comfortable for 1 person eachi felt comfortable as soon as we arrivedCleanliness:
it was clean and neatinside was clean and well furnishedclean well appointed altogether great for usnicely decorated very clean beds comfortable with lots of pillows plenty of towelsclean comfy and convenient to all the area offersHost:
the instructions and communications with the owner were flawlessivone's home had everything you could need and ivone was incredibly responsive throughout our stayivone was very responsive to text messagesivone is a very gracious host and this house is quite niceivone was immediately responsive to all my questionsRead more reviewsLocation:
the central location was helpful to get to everythingeverything was great perfect location and safe neighborhoodivone's place is a cute home in a great locationivone's place is incredibly cute and cozylocation is excellent - easy access to cumberland lavale frostburg
4. Townhouse in historic Downtown Cumberland
This vintage townhouse is two blocks away from Downtown Cumberland, 10 minutes to Western Maryland Scenic Railroad and C&O Canal bike trails. This registered historic home was recently renovated to accommodate up to eight guests. It has three spacious bedrooms with two double beds and a double bunk bed. All rooms have air-conditioning, free WiFi, heating, closets, and desk space. The TV has Roku & Hulu channels and HDMI ports for computer devices. The full bathroom has a tub with shower, hot water, and free essentials. Guests enjoy use of the fully stocked kitchen, laundry facilities, free parking, and the hot tub at the back of the house. The wide terrace has an awesome view of outdoor greenery. Pets and smoking are not allowed. Luggage dropoff and long-term stays are allowed.
Cumberland, Maryland, United States
10.8 km (6.8 mi) from Rocky Gap State ParkAccommodates: 8
Top guest reviews
Amenities & Room:
the house was modest comfortable and fit our needsheidi and matt's place is charming and comfortablewe enjoyed the comfortable living area on the main level; plenty of space to relaxwe slept well--all was clean and the living room couch was super comfortableloved the hot tub and enjoyed a comfortable nights sleepCleanliness:
very clean and well appointedthe space was cleanthe place was super clean and easy to accessit was clean and had adequate space for all of usthe place was clean there was clear communication and it was convenient to downtownHost:
wonderful hosts and very nice homewonderful hosts good communicationheidi and matt were great hostsmatt & heidi were fantastic hosts and we loved their little townhouse in cumberlandthey provided a comprehensive guide for enjoying the town which was really helpful during the stayRead more reviewsLocation:
great location walking distance to restaurantsgreat location to downtown cumberlandawesome place very well locatedwonderful location for a group of friends to spend the weekend during a festival near townthere place was wonderful the location wa perfect and right near to everything we needed
5. Jacob's Cottage LLC (from USD 90)
This old-world Cape Cod-style cottage sits on a hill in Allegany County’s Appalachian Mountains, 6 miles (9.66 km) from Cumberland Center, Canal Place, Potomac River, Rocky GAP Resort, and other town attractions. A well-kept two-acre (0.8-hectare) yard surrounds it with the lush wild forest in the background. The well-decorated cottage has two floors. The main floor has a fully equipped kitchen, dining area with indoor fireplace, carpeted living room, and laundry facilities. Eight guests can sleep comfortably in three spacious, fully air-conditioned bedrooms that have several double and single beds with thick cushions. The full bathroom has free toiletries and hot water. There’s a screened-in porch where you can enjoy mountain views. Free parking is available.
Cumberland, Maryland, United States
6.42 km (4.0 mi) from Rocky Gap State ParkAccommodates: 8
Top guest reviews
Amenities & Room:
the wifi is super fast and the kitchen is well appointedwe did not miss tv or wifi at all and will definitely book againif you are looking for a clean comfortable cottage in quiet peaceful surroundings then jacob's cottage is for youplenty of room for friends and relaxingmy two daughters three grandchildren and i were very comfortableCleanliness:
we enjoyed the peace and quiet and how clean everything wasthe cabin is clean spacious comfortable and easily assessiblethe house was clean and exactly what we were looking fora peaceful and clean home with beautiful art workthe house is super cleanHost:
daniel was a great hostowners were easy to contacthosts were very responsive and accommodatingthe hosts were very responsive and went over and above to help us feel at homegreat property and great ownersRead more reviewsLocation:
beautiful location filled with wildlifethe location of the house is amazing - quiet - peaceful -the place is in a beautiful and quiet location and has a very comfortable homey vibe insidewonderful place for an evening away just a few minutes from rocky gapextremely quiet and peaceful a great get away from suburban rush
6. Cumberland Street House — easy access to GAP (from USD 129)
This lovely 1908 home is a quarter of a mile away from Great Allegheny Passage (GAP) and half a mile away from Downtown’s fancy restaurants and shops. The historic district, Maryland Scenic Railroad, and the theater are minutes away. Six people have exclusive use of this updated old-fashioned house. The fully stocked kitchen, dining area, living room, and laundry facilities are all on the ground floor. The house has a full bath on the second floor and a half bath on the ground floor, both with free toiletries. The two upstairs bedrooms are simply furnished with thick cushioned beds, air conditioning, heating, and free WiFi. Relax on the covered porch or watch a show on the smart TV in the living room. Kids and pets can play in the fenced-in yard at the back of the house. There’s parking for cars and bikes on the property.
Cumberland, Maryland, United States
11.4 km (7.1 mi) from Rocky Gap State ParkAccommodates: 8
Top guest reviews
Amenities & Room:
we experienced air conditioning in all of our rooms and the home was nice and roomygiven the duration of my stay i especially appreciated having a full kitchen and a washer/dryerlots of room for a good sized group to spread outthe bed was unbelievably comfortableCleanliness:
very clean and good communicationeverything was really clean and clutter freehome is clean and comfortableeverything was super clean and comfortablebeautifully clean in all areas and very comfortable and spaciousHost:
shari was the perfect hostowner shari very responsive to questions very nice roomy homeshari is a extremely responsive and friendly hostgreat quick communications with the hostgreat host and nice houseRead more reviewsLocation:
wonderful location easy walking distance to downtownbeautiful place close to downtown cumberlandreally liked the locationgreat location from the trail and downtown cumberlandthe location is great; quiet at night but close to anything you need
7. A gorgeous Victorian mansion in the downtown area
Situated in the downtown area on Washington Street, this Victorian mansion looks gorgeous from the outside. Originally built in 1890 for US Senator Wellington, the mansion features two spacious bedrooms and one bathroom for up to four people. The mansion is especially suitable for those traveling with young children, as there are a collection of board games, along with children’s toys for their use.
If you are interested in knowing a little bit about the local history, you can find some books on this topic in the home. The kitchen comes with vintage dining furniture and decor items and you are going to love it.
Cumberland, Maryland, United States
11.67 km (7.3 mi) from Rocky Gap State ParkAccommodates: 4
Top guest reviews
Amenities & Room:
the air conditioner was on and the place nice and cool when i arrivedwe were happy that there was consistent wifi available since there is no televisionthe apartment was as described and check in was secure and convenientthe kitchen is efficient with full size appliancesthe apartment is nicely secluded and comfortable though the access to it is a bit of a mazeCleanliness:
sean’s place was clean and accommodatingit is clean and welcomingthe apartment was clean and as expectedquaint clean apartment loaded with charm and conveniencethe apartment is clean and cozy and the two rooms are spaciousHost:
host was very communicative and helpfulour host was great responding to us quickly and efficientlythe owner was quick to respond and help with anything i neededhe was quick to respond and helpfulthe host was very helpful and offered suggestions for things to doRead more reviewsLocation:
cool location in historic district about a 10-minute walk to cumberland's downtowngreat location to downtown areagreat location and great spaceperfect location to visit cumberland essentialsgreat location to center of town tho
8. Private basement bed for travelers
This private basement is still a work in progress, but its location is ideal for bikers and travelers who need a place to rest during a long trip. The house is in Frostburg, near GAP, FSU, and I-68. The private entrance at the side of the house leads to the basement. The room is a wide open space featuring a huge double bed for two guests with a fan, heating, a mini ref, microwave, coffeemaker, and a half bath. The sofa bed sleeps an additional two guests. If you need privacy, you can just draw the curtains to define your space. The full bathroom and kitchen on the main floor are shared with the owners. Guests are provided free WiFi, free parking, and free essentials.
Frostburg, Maryland, United States
24.75 km (15.4 mi) from Rocky Gap State ParkTop guest reviews
Amenities & Room:
space heater was used which worked very wellit was very helpful that she allowed me to use her washer/dryer and kitchengreat heated room and comfortable bedthe space was nice and the bed comfortableCleanliness:
home was clean and as describedit was clean comfortable and well maintainedclean comfortable and enjoyable stayheather's place was very clean and i enjoyed my stay thereit was quiet and clean - we got a great night's sleep between two six-hour drivesHost:
the host is thoughtful and responsivegreat host and cool placeheather is a great hostheather was a great hostheather really is a super hostRead more reviewsLocation:
the location was perfectsecure place for my bike and a comfortable bedgreat value nice and quiet locationthis was a great location to spend the night for a great pricevery convenient location and a most helpful host
9. Decatur Guest House
Bikers will love this room in a newly remodeled home with lots of amusing bike-related decorations. It’s near Cumberland downtown, Allegany College, a hospital, and bike trails. It’s the perfect start-off or rest point of a long bike ride. Nine guests will fit snuggly into this huge bedroom that can be rented on a monthly, weekly, or nightly basis. It has nine cozy single beds, free WiFi, air conditioning, central heating, laptop space, and smart TV. The two private bathrooms guests can use have rainfall showers, hot water, and free essentials. Guests may use the fully equipped kitchen, living room, and laundry room. There’s free parking on the property.
10.54 km (6.6 mi) from Rocky Gap State Park
10. Historic Hitchins house: King bed with en-suite bath
This postcard-pretty Victorian home is minutes away from elegant restaurants, wineries, music, and shops. It’s a few blocks to the GAP and Frostburg State University. The owners retained the old-fashioned décor of the home that was given a fresh coat of paint and modern amenities. Two guests can rent one private bedroom. The huge fully carpeted room has a king bed, closet space, desk space, armoire, a fully stocked mini-ref, coffeemaker, TV with Roku, and seating area. The en-suite bathroom has hot water and free essentials. Guests may use the kitchen, library, parlor, and piano room. Use of laundry facilities is by request. Private and off-street parking is available.
Frostburg, Maryland, United States
24.09 km (15.0 mi) from Rocky Gap State ParkTop guest reviews
Amenities & Room:
great amenities in the room including snacks and all manner of toiletriesa large room fresh coffee & drinks private bath & off street parkingthe room is very private and is outfitted with a roku tv which is really nicethe room was pleasant and the king bed comfortablethe bed is probably the most comfortable i've ever slept inCleanliness:
everything was very clean and cozythe space was very clean and welcomingthe room was very clean and quietspotlessly clean tastefully furnished with quality bedding and a nice comfy mattressthe room is always spotless and comfortableHost:
lovely home and super hostsbe sure to communicate with the hosts if you have any questions or commentseasygoing friendly hostslisa and joe are wonderful hostshosts were super friendly and welcoming to their beautiful homeRead more reviewsLocation:
great location to explore frostburgclose to the gap trail and various other points of interest in western marylandthe house is beautiful and in the perfect location to walk through frostburgthis was the perfect place to stay for the weekend it’s easy to walk to from downtown frostburglovely room super comfortable bed and the perfect location right on main street
11. — Beautiful room close to Downtown Cumberland
Guests will love this private room in a restored classic home. It’s near Downtown Cumberland, Baltimore Street promenade, C&O canal, shops, and restaurants. The owners retained the classic details of its structure and updated the look with modern furnishings. The second-floor bedroom is earth-toned and can sleep two travelers comfortably in its two single beds. Guests are welcome to use the fully equipped kitchen and dining area to cook and eat their meals. They can relax on the wide front porch and back patio. The marble tiled bathroom is shared with the owners of the house. Enjoy use of free WiFi, laundry facilities, TV, and free street parking.
Cumberland, Maryland, United States
12.09 km (7.6 mi) from Rocky Gap State ParkAccommodates: 2
Top guest reviews
Amenities & Room:
the bed was comfortable i had an extra portable heater offered to me if i was coldthe beds were highly comfortable and my sleep was wonderful on themcomfortable stylish place in a historic part of townCleanliness:
very clean and comfortableclean and mostly tidy if not spotlessalways clean and comfortableclean clean clean extra touches plus tips on local placesthe space is clean and aesthetically charmingHost:
david was very responsivedavid was a great hostdavid is such a pleasant hostlovely digs thoughtful host quaint towndavid is a great host very accommodatingRead more reviewsLocation:
nice location close to townnice place close to city centerthe house is conveniently located in a walking distance to all the attractions of downtown cumberlandnice accommodating house in a good locationit was in the heart of down town a great place to stay loved it
Relaxing stays with a vintage vibe!
Vintage homes, even if renovated, still retain a classy and old-fashioned vibe that is both cozy and relaxing! These homes offer respite to travelers who want to escape from the stresses of the concrete jungle. You’ll find that here when you rent one of the Airbnb homes in Cumberland.
History
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