
Cottage vacation rentals in Cumberland
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Cumberland
Guests agree: these cottages are highly rated for location, cleanliness, and more.

Hidden Hill - Cozy Downtown Cottage with Hot Tub!!
Hidden Hill is a renovated 1880’s cottage tucked away just above historic downtown Berkeley Springs. Xfinity high speed internet! Literally steps from spas, restaurants, art, antiques, and nightlife, this cottage also feels hidden just above downtown. Hidden Hill is a great spot to stay while enjoying everything Berkeley Springs has to offer. Explore everything West Virginia has to offer during the day, then retreat to Hidden Hill for the convenience of restaurants and bars at your doorstep.

Sisters on Lincoln
Dog and family-friendly spacious cottage in the Laurel Highlands centrally located to so many attractions! Uptown Somerset is blocks away, it's just 15 minutes to Hidden Valley or 30 to Seven Springs resorts! Visit Somerset Lake, the Flight 93 Memorial, State Parks, Covered Bridges, Idlewild Theme Park, Falling Water, Ohiopyle white-water rafting, hiking, & biking trails, breweries, distilleries, Festivals, wineries & great antiquing! Unwind at night by the cozy fireplace or outside firepit!

The Cottage on the Hill
Nestled against a hillside, at the end of a small city lane, sits a charming private retreat. Park in one of your reserved spaces and step down to a unique retreat high above the city to enjoy a vintage cottage with modern amenities. Walk to Historic Cumberland, enjoy local and regional attractions, or stay in and grill, build a fire, or play pool, poker, board or yard games. Well appointed, fully equipped, and with a beautiful view, come relax and enjoy this one of a kind location.

Mountain Oasis Cottage
Our Cottage is located at the base of a mountain on a dead end road it is very tranquil with a lot of deer that feed in the back yard. We are 15 minutes from the city of Cumberland Maryland where the “Western Maryland Bike Trail” is located and 30 minutes from historic Bedford, PA. The Cottage has two bedrooms that each feature queen size beds, one living room with a pull out queen size sofa bed, and a sitting room with a full size pull out sofa bed. Heated and cooled w/ mini splits.

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.

Purple Kangaroo Cottages
Lord Brigerton’s cottage has nothing on this one as it is not a fairytale! The cottage offers a stylish/warm atmosphere for couples to connect with each other and the outdoors. The outdoor fireplace/pit gazing at the stars is must see entertainment. This intimate getaway will provide for making wonderful memories in a picturesque, relaxing location free from the bothers of normal life, with WIFI. Cottage can be used as a venue, pricing is then negotiable. NO SMOKING

Avery Pines Cottage
Set apart on our five-acre property, this newly constructed cottage sits in a quiet location about 135 feet from the main house, with trees providing a natural privacy buffer (especially in the spring, summer, and early fall). Enjoy Wi-Fi, a queen bed, kitchenette, comfy living area, and a deck with woodland views. Safe, quiet, and scenic—just 20 minutes from historic downtown Winchester for shopping, dining, and local attractions—your ideal private retreat.

Cheerful 3 bedroom cottage with amazing views
If you are looking to get away and relax in a peaceful country setting, in the beautiful western Maryland mountains, this is the place for you. Hiking and scenic overlook close by. Locust Post Brewery with live entertainment and food just minutes away. Rocky Gap Casino and Golf resort just a short drive. Historic downtown Cumberland, MD, home of the Western MD Scenic Railroad, as well as shops and dining is approximately a 20 minute drive from the house.

*Deep Retreat* Fenced Dog Yard-Hot Tub-Fire Pit
Deep Retreat Cottage is 10 minutes from Wisp resort and most Lake activities! Boat Slip, Fire Place, Hot tub, fire pit, wifi and Streaming smart hdtv's. Awesome outdoor area with corn hole and horse shoes. The Cottage is Comfy, Cozy and ready for your Deep Creek Lake getaway. 2 Bedroom, 2 bath with loft sleeps 8 adults comfortably with amenities including Fire Place, Hot Tub, Fire Pit, WIFI and Gas and Charcoal Grills. Minimum Rental Age - 25

Emma's Stone Cottage
Relax and unwind in the privacy of this wonderful stone cottage, which sits on 15 acres. In addition, it is located only 2.5 miles from I-81 and approx 10 miles from Winchester Medical Center, Old Town Winchester, Shenandoah University and much more. Our cottage has everything you need for a peaceful and enjoyable stay including full kitchen, central air, water softener, HD smart televisions, Wifi, outdoor firepit and more.

The 3R's River, Relaxation, Retreat + hot tub
Rustic river cabin on Cacapon River on stilts only 4 steps away from the river .Fishing ,kayaking, swimming, camp fires ,grilling and relaxing from riverside deck over looking the Cacapon River. Capon Bridge W.V is a little over a mile away with restaurants , shopping, artesian market and fresh market with local wines. Plus see the occasional American bald Eagle.

Last Rodeo Cottage
Our cottage is private where guest can relax; Looking to spend some quiet time out of the city. Close to D.C.and the Historic site of surrounding areas. Close to Charlestown Casinos. Our home is right off I- 81 This cottage is Handicap accessible from private parking to shower and amenities. Lovely park like setting shared with our family pets.
Popular amenities for Cumberland cottage rentals
Cottage rentals with a hot tub

Wide Open Spaces - 4 Bedroom Cottage

Play & Stay near State Parks & Seven Springs

2BR Spacious House w/private hot tub

Changes in Altitude - 4 Bedroom Cottage

Sunset View: Lakefront Pet-Friendly | Dock

Just Chillin' - 4 Bedroom Cottage

Almost Heaven - 4 Bedroom Cottage

Vital Idyll - 4 Bedroom Accessible Cottage
Pet-friendly cottage rentals

Sky Valley Lake access home/Quiet Cozy

Country farmhouse with 50 acres and private pond

Hawks Nest Stay

Lois Lane Stream side Cottage w/ Swimming Hole

Deep Creek Lake Cozy Cottage (Dog Friendly)

Wooded Mountain Retreat near Creek

Modern 3BR Farmhouse in the Country
Private cottage rentals

The Hillside Hideaway

*Deep Retreat* Fenced Dog Yard-Hot Tub-Fire Pit

Brookside Cottage

The Cottage on the Hill

The River House

The 3R's River, Relaxation, Retreat + hot tub

Hidden Hill - Cozy Downtown Cottage with Hot Tub!!

Sisters on Lincoln
Quick stats about cottage rentals in Cumberland

Nightly prices starting at
Cumberland vacation rentals start at $232 CAD per night before taxes and fees

Verified guest reviews
Over 270 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Cumberland rentals

5 Average rating
Cumberland stays are highly rated by guests—averaging 5 out of 5!
Destinations to explore
- Norfolk Vacation rentals
- Plainview Vacation rentals
- New York City Vacation rentals
- Tuckahoe Vacation rentals
- Greater Toronto and Hamilton Area Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Mississauga Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Rentals with a washer and dryer Cumberland
- Cabin rentals Cumberland
- Family-friendly rentals Cumberland
- Rentals with a patio Cumberland
- Rentals with outdoor seating Cumberland
- Apartment rentals Cumberland
- Pet-friendly rentals Cumberland
- House rentals Cumberland
- Cottage rentals Maryland
- Cottage rentals United States
- Wisp Resort
- Fallingwater
- Seven Springs Mountain Resort
- Berkeley Springs State Park
- Ohiopyle State Park
- Cacapon Resort State Park
- Whitetail Resort
- Blue Knob All Seasons Resort
- Green Ridge State Forest
- Rock Gap State Park
- Museum of the Shenandoah Valley
- Deep Creek Lake State Park
- Swallow Falls State Park
- Fort Ligonier
- Old Town Winchester Walking Mall
- Laurel Hill State Park
- Fort Necessity National Battlefield
- Laurel Ridge State Park




