
Cottage holiday 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.

COZY+SEXY Private Country Escape! HOT TUB & Views~
Look no further for privacy, intimacy, & fun~ Foxy is your perfect escape, located in the Shenandoah Valley & surrounded by a 1000 private acres but only 10 minutes from downtown Winchester. Offering a uniquely glamorous experience, surrounded by all the beauty of nature. Indulge in luxury & tranquility with amenities including your own private patio with hot tub and million dollar views of the Blue Ridge Mountains. Inside, a full chef's kitchen leading to a sexy, opulent master bedroom suite...

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.

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.

Nice and Cozy Rental
Great cottage nestled in the mountains on 63 wooded acres with barn, spring house and main house. Cottage has fireplace with first ring of logs provided. Two Smart TVs , VCR and DVD player with tapes and DVDs provided. Large deck and patio furniture off the living room with private woodland views and a babbling brook. Outdoor fire pit also provided. Close to Fallingwater, Ohiopyle and Seven Springs. Pet friendly (up to 2) and beautiful hiking trails in our woods.

Entire Cottage w/ Additional Creek Cabin
****Please read entire description of property*** Main cottage (available year-round) - 1 bedroom, 1 sleep sofa in living room, 1 full bath, 1 half bath off kitchen Additional creek-side cabin (only available April 1- November 1 - $85/night plus $50 cleaning fee) - 1 bedroom, sofa, 1 full bath, dry kitchenette We never rent the creek-side cabin separately from the main cottage. If you do not need to rent it, you will still have access to the creek-side deck.

*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

Stone Haven
Welcome to Stone Haven — a cheerful stone cottage just minutes from Deep Creek Lake. Guests love Stone Haven for its charm, cleanliness, thoughtful touches, cozy atmosphere, and convenient location near the lake, Wisp Resort, hiking trails, restaurants, and local shops. Whether you’re visiting for lake days, skiing, hiking, or a quiet weekend away, Stone Haven offers a relaxing and comfortable place to return to after exploring the area.

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 cottage rentals in Cumberland
Cottage rentals with a hot tub

House, 2 Bedrooms, 2 queen sofa bed

Potomac River Retreat

Dock Holiday-Lake access with a boat slip

Indian Head Retreat

Play & Stay near State Parks & Seven Springs

The Rustic Cottage

Sunset View: Lakefront Pet-Friendly | Dock

Just Chillin' - 4 Bedroom Cottage
Pet-friendly cottage rentals

Game room| W/D| Fire pit| Full Kitchen| BBQ| Walk!

Brookside Cottage

Hawks Nest Stay

Purple Kangaroo Cottages

Modern 3BR Farmhouse in the Country

Margaret’s Meadow

Pet friendly-Cottage in the Woods

Secluded Mountain Top Retreat | Stunning Views
Private cottage rentals

Cozy Ohiopyle/Fallingwater Cabin Hot Tub Fire Pit

Deep Creek Lake A Country Life Chateau

Luxury Cottage near Fallingwater

The Hillside Hideaway

Changes in Altitude - 4 Bedroom Cottage

Almost Heaven - 4 Bedroom Cottage

Whispering Pines/Near Deep Creek Lake/No Fees

Vital Idyll - 4 Bedroom Accessible Cottage
Quick stats about cottage rentals in Cumberland

Nightly prices starting at
Cumberland holiday rentals start at £126 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 Holiday rentals
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Mississauga Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- House rentals Cumberland
- Cabin rentals Cumberland
- Flat rentals Cumberland
- Pet-friendly rentals Cumberland
- Family-friendly rentals Cumberland
- Rentals with a washing machine and dryer Cumberland
- Rentals with outdoor seating Cumberland
- Rentals with a patio 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
- Blue Knob All Seasons Resort
- Whitetail Resort
- Rock Gap State Park
- Green Ridge State Forest
- Laurel Hill State Park
- Swallow Falls State Park
- Fort Ligonier
- Shawnee State Park
- Deep Creek Lake State Park
- Old Town Winchester Walking Mall
- Laurel Mountain Ski Resort
- Laurel Ridge State Park
- Fort Necessity National Battlefield
- Museum of the Shenandoah Valley
- Lodestone Golf Course
- Linn Run State Park
- Western Maryland Scenic Railroad





