Holiday rentals in Ridgeley

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.

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, 58 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, 471 reviews

Flat 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, 190 reviews

Flat 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.

4.9 out of 5 average rating, 544 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, 111 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, 306 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.

Guest house in Cumberland

5 out of 5 average rating, 58 reviews

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.

Superhost

Flat in Cumberland

4.88 out of 5 average rating, 25 reviews

Downtown Rustic Refuge - Walk or Bike Everywhere!

This Comfy 2nd Flr (Unit B) Flat provides access to everything! Explore local attractions or take day trips to Luray Caverns(VA), Smithsonian Museums(DC), or the world's largest Bicycle Museum(PA) all within 2 hours. Our place is perfect for any stay - pleasure, festivals, work, or just passing through. Enjoy the GAP trail and more outdoor adventures! We have everything you need for a comfy stay. Let us know if you need kid accommodations.

4.92 out of 5 average rating, 132 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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Other great holiday rentals in Ridgeley

5 out of 5 average rating, 19 reviews

Downtown on Centre

BrittneyRating, 5 stars18 months ago

I can't say enough good things about this AirBnB. Impeccable design and personal touches everywhere. Seasonal elements were subtle and beautiful. All the furnishings, textiles and kitchenware are high end and high quality which is rare in an AirBnB. The photos of the space don't do it justice! The location is great - less than a 5 minute walk to the train station and several great restaurants. Door Dash was fast/easy when we didn't want to go back out. Parking was easy right out front. If we do the Polar Express experience again this will definitely be the place to stay!

5 out of 5 average rating, 23 reviews

Home in La Vale

CJ’s Escape Great location & just like home

StacieRating, 5 stars1 week ago

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, 41 reviews

Flat in Bedford

Private Studio Apartment - Own Entry

MeghanRating, 5 stars1 day ago

What a comfortable spot—perfect for a good night’s rest after a weekend of camping. Kevin was incredibly responsive and accommodating. He even allowed me to have a late checkout and gave me a ride when I was unable to get an uber.

4.97 out of 5 average rating, 39 reviews

Guest house in Ellerslie

Cottage Escape in the Allegany Mountains

AustinRating, 5 stars3 months ago

This was by far my most pleasurable stay I have ever had booking with airbnb. The host was friendly, responsive, and ensured that anything we could ask for was available. I would 100% recommend others to stay here. From the moment we walked in it felt like a true home. The furnishings we cozy and the aesthetic was far above the average. It felt like a fancy hotel stay. I would have loved to stay for a month or even rent from this owner 😅

5 out of 5 average rating, 54 reviews

Townhouse in Oldtown

Sierra Farmstead - Guest House

RebeccaRating, 5 stars2 days ago

Great stay at Sierra Farmstead. Very comfy beds (the full and queen); well lit, easy to navigate and great bathroom. Great jumping off point for exploring the natural beauty of the area. Hosts were responsive. Our pup was with us and also enjoyed!

Flat in Cumberland

4.75 out of 5 average rating, 148 reviews

The Caverne'-quaint EFF near C&O Canal, GAP & UPMC

JamesRating, 5 stars3 weeks ago

Thank you Allison for your hospitality. The accommodations are definitely unique, but functioned well for our situation. The shed was helpful because we were able to lock up our bicycles and have them out of view. Your location is good and works well for bicycle tourists on the C and O towpath and the GAP bike trail. Thanks again and I wish you continued success with your Airbnb!