Holiday houses in Cumberland

4.94 out of 5 average rating, 253 reviews

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.

5 out of 5 average rating, 109 reviews

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.

4.92 out of 5 average rating, 26 reviews

Saratoga Stays! Close to C&O!

Welcome to our charming three-bedroom home located in Cumberland, MD. Perfect for families or small groups, our cozy retreat sleeps up to 5 guests comfortably. Enjoy the convenience of a spacious yard, ideal for relaxation or outdoor gatherings. With laundry facilities on-site, your stay is made even more convenient. Cyclists rejoice – we offer ample space to store bicycles securely. Experience comfort & convenience in the heart of Cumberland at our inviting home. Close to downtown & canal!

4.95 out of 5 average rating, 57 reviews

Loft in Cumberland

Historical loft, 2 Blocks from Trail & Downtown

When you enter your loft apartment you will have an interior space to secure your bikes. After a fun day on the C&O or GAP trail you will enjoy a shower, a cup of local Basecamp coffee, and restful sleep Conveniently located 2 blocks off a trail entrance. Downtown restaurants only a 5 minute drive Included in your room is a kitchen sink, microwave, fridge/freezer, toaster and 12 cup coffee pot with local Basecamp coffee in regular & decaf, & tea Keyless entry, entire place to yourself

4.99 out of 5 average rating, 466 reviews

Apartment in Cumberland

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.

4.97 out of 5 average rating, 188 reviews

Apartment in Meyersdale

Country Home

Relax with family, friends, or enjoy a solo retreat at this peaceful place to stay in the country. Chestnut House was built in the early 1940s, with Wormy Chestnut wood everywhere! It is a unique home, with an apartment built over a garage / wood working shop.. then connected to the main house later. This space available to rent is separate and fully functional from the main house where we live. Enjoy 2 bedrooms, 1 bathroom, full kitchen and living area.. along with the large outdoors!

4.84 out of 5 average rating, 157 reviews

Charming 1907 Home in Historic Downtown Cumberland

This charming 1907 home is located just blocks from the main pedestrian street in Historic Downtown Cumberland and a 10 minute walk from Canal Place, the C&O Canal Great Allegheny bike trails, and the Western Maryland Scenic Railroad. The remodeled interior is equipped with all the modern conveniences, including a large kitchen and bathroom with large tub and seven-head shower. The house maintains its historic charm with exposed brick and has a balcony, back patio, and yard space.

5 out of 5 average rating, 108 reviews

Cabin in Springfield

1832 Historic Washington Bottom Farm Log Cabin

Welcome to our renovated 1832 Log Cabin on our 300+acre Certified Organic farm. Guests can use our river frontage to fish, canoe, kayak, tube, or gather by the fire pit. We have mountain views, dark night skies revealing stars, planets, and the Milky Way, plus great sunsets. Wildlife includes deer, fox, bear, turkey, eagles, and owls, to name only a few. Lots of History here: site of a French & Indian fort, an early Indian Burial Mound, and the Hosts' historic plantation home.

4.89 out of 5 average rating, 542 reviews

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.

4.9 out of 5 average rating, 108 reviews

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.

4.86 out of 5 average rating, 304 reviews

Home in Frostburg

Allegany Connection

NOTICE: extra santizing of hand touching areas in place for your protection. This eclectic 2-story duplex, late 18th century structure has both old and new charm. Single BR & bath upstairs; LR and Kit downstairs. Only 1 block from Main St. restaurants & unique shops. All are welcomed. Please bring your own infant bed. Sorry no pets. Free reserved parking for 1 vehicle & fast Wi-Fi. Instant booking is on. ABSOLUTELY NO SMOKING, or any kind is permitted inside our home.

4.92 out of 5 average rating, 127 reviews

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.

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Popular amenities for Cumberland holiday rentals

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Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Cumberland

Superhost

Apartment in Midlothian

4.82 out of 5 average rating, 11 reviews

Studio Apartment near FSU

DanRating, 5 stars2 weeks ago

it was lovely, quiet, clean, easy to access and communicate. highly reccomend. right next to a small stream that was lovely.

5 out of 5 average rating, 23 reviews

Home in La Vale

CJ’s Escape Great location & just like home

StacieRating, 5 starstoday

This is the second time we have stayed at Jean’s and we love it! The house is beautiful and inviting. The yard is huge with a great fire pit. Jean is always very communicative and lovely. We will be back again!

5 out of 5 average rating, 26 reviews

Spacious Parkside Oasis!

CindyRating, 5 stars1 week ago

Great stay for a wedding weekend! We were able to bring our pup and the house was much larger than others rented by my family and we fortunately had 2 bathrooms. Host provided everything needed.

4.94 out of 5 average rating, 96 reviews

Great Location, Spacious, Comfy 2 bdrm 3 bed home

JakeRating, 5 stars3 weeks ago

Great stay! Everything labeled clearly and very good communication with the host.

4.98 out of 5 average rating, 93 reviews

Cottage in Green Spring

The River House

RickRating, 5 stars4 weeks ago

If you are looking for a secluded little get-away with a great host, this is the spot. Unfortunately these reviews only allow 1000 characters otherwise I would write a novel of a review for Rachelle and The River House. I stayed for 6 weeks with my dog in April and May watching Spring bloom. How beautiful! I was able to float down the river, see wildlife, go fishing, get fresh free-range organic chicken eggs, eat outside in the fresh air, hangout with one of the neighbor dogs, watch hummingbirds, and enjoy fires at night in the firepit and more! They recently added Starlink for the internet wifi and it was blazing fast. It is perfect for working remotely (video calls) and streaming. The beds and pillows are comfy. The water is hot. The place is clean. Rachelle is a top-tier host and super friendly, considerate and responsive. We had a couple of minor issues and she resolved them ASAP. If you're not used to the buggy woods keep that in mind, especially during the warmer months.

4.9 out of 5 average rating, 52 reviews

Cozy Cottage

AlecRating, 5 stars1 week ago

Donna was great! Easy check in and place was clean!