
Cottage holiday rentals in Cumberland
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Quick stats about cottage rentals in Cumberland

Nightly prices starting at
Cumberland holiday rentals start at $239 AUD per night before taxes and fees

Verified guest reviews
Over 280 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Cumberland rentals

5 Average rating
Cumberland stays are highly rated by guests—averaging 5 out of 5!
Top-rated cottage rentals in Cumberland
Guests agree: These cottages are highly rated for location, cleanliness and more.

Country farmhouse with 50 acres and private pond
Escape city life to this peaceful and relaxing country farmhouse on 50 hike able acres with spring fed pond for paddling, fishing and swimming. In the evenings, relax by the fire pit or on the deck while the kids catch fireflies, play games or watch a movie. You’ll feel a million miles from your hectic everyday life, yet it’s only 10-15 minutes to pick up groceries or head out for dinner at The Hen House or Cornucopia. Note: Hiking 50 acres not allowed during hunting season which starts 10/1.
4.92 out of 5 average rating, 59 reviews
Blue Skies Ahead: Charming 3 bdrm Cottage w/patio
Our charming 3-bedroom cottage has everything you need for your Berkeley Springs trip. The home comes with fast Wi-Fi and self check-in. It backs to woods for privacy and views of the local wildlife. Visit the quaint shops and medicinal springs at the Berkeley Springs State Park or book a massage! Our home boasts 1.5 baths, a full newly renovated kitchen and washer/dryer. It is within driving distance to several popular museums, hikes, and cafes. An ideal base to explore Berkeley Springs.
4.73 out of 5 average rating, 75 reviews
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.
4.93 out of 5 average rating, 517 reviews
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.
4.99 out of 5 average rating, 204 reviews
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.
4.99 out of 5 average rating, 125 reviews
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.
4.98 out of 5 average rating, 130 reviews
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 residence where we live, 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.
4.97 out of 5 average rating, 70 reviews
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.
4.92 out of 5 average rating, 106 reviews
*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
4.92 out of 5 average rating, 296 reviews
River Front Retreat *HotTub-FirePit-Kayaks*
Unplug and unwind. *River Front *Steps away from Cacapon River with easy access *Hot tub facing river *Kayaks with Life vests on property *Decks with BBQ and dining Alfresco *Two Fire pits: River Front Wood Fire pit and Propane on the Deck *Yard games/board games *Wi-Fi and Smart TV. *Comfy beds/black out curtains *Pet-Friendly ($25/day for 2 dogs) ***pet policy below Come step into nature and nurture your spirit at our riverfront haven.
5.0 out of 5 average rating, 111 reviews
Lakefront Cottage with Spectacular Views
Lakefront cottage with tremendous views and private dock . Home is on a quiet lane with pedestrian friendly activity. This is an original lakefront cottage that has been completely updated. Swim or fish from the dock or shoreline, bring your own boat, or use the two sea kayaks provided. Well equipped kitchen. Quaint, updated cabin offers relaxing atmosphere, serene family environment. No large groups or partiers allowed.
4.93 out of 5 average rating, 45 reviews
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.
4.97 out of 5 average rating, 234 reviewsPopular amenities for Cumberland cottage rentals
Cottage rentals with a hot tub

Sunset View: Lakefront Pet-Friendly | Dock
4.67 out of 5 average rating, 24 reviews
River Front Retreat *HotTub-FirePit-Kayaks*
5.0 out of 5 average rating, 111 reviews
Hidden Hill - Cozy Downtown Cottage with Hot Tub!!
4.93 out of 5 average rating, 517 reviews
The 3R's River, Relaxation, Retreat + hot tub
4.97 out of 5 average rating, 234 reviews
*Deep Retreat* Fenced Dog Yard-Hot Tub-Fire Pit
4.92 out of 5 average rating, 296 reviews
Potomac River Retreat
4.67 out of 5 average rating, 58 reviewsPet-friendly cottage rentals

Sky Valley Lake access home/Quiet Cozy
4.65 out of 5 average rating, 62 reviews
The River House
4.98 out of 5 average rating, 130 reviews
Mountain Oasis Cottage
4.99 out of 5 average rating, 125 reviews
River Front Retreat *HotTub-FirePit-Kayaks*
5.0 out of 5 average rating, 111 reviews
Hidden Hill - Cozy Downtown Cottage with Hot Tub!!
4.93 out of 5 average rating, 517 reviews
*Deep Retreat* Fenced Dog Yard-Hot Tub-Fire Pit
4.92 out of 5 average rating, 296 reviews
Wooded Mountain Retreat near Creek
4.84 out of 5 average rating, 332 reviews
Brookside Cottage
4.96 out of 5 average rating, 134 reviewsPrivate cottage rentals

Brookie Cottage on the Savage River
4.92 out of 5 average rating, 90 reviews
The Hillside Hideaway
5.0 out of 5 average rating, 80 reviews
The Cottage on the Hill
4.99 out of 5 average rating, 204 reviews
The River House
4.98 out of 5 average rating, 130 reviews
Mountain Oasis Cottage
4.99 out of 5 average rating, 125 reviews
River Front Retreat *HotTub-FirePit-Kayaks*
5.0 out of 5 average rating, 111 reviews
Hidden Hill - Cozy Downtown Cottage with Hot Tub!!
4.93 out of 5 average rating, 517 reviews
The 3R's River, Relaxation, Retreat + hot tub
4.97 out of 5 average rating, 234 reviewsDestinations to explore
- New York Holiday rentals
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- Seven Springs Mountain Resort
- Fallingwater
- Wisp Resort
- Ohiopyle State Park
- Berkeley Springs State Park
- Rock Gap State Park
- Swallow Falls State Park
- Deep Creek Lake State Park
- Cacapon Resort State Park
- Laurel Hill State Park
- Green Ridge State Forest
- Blue Knob All Seasons Resort
- Fort Ligonier
- Fort Necessity National Battlefield
- Old Town Winchester Walking Mall
- Laurel Ridge State Park
- Whitetail Resort
- Museum of the Shenandoah Valley
- Linn Run State Park
- Laurel Mountain Ski Resort
- Shawnee State Park
- Lodestone Golf Course
- Western Maryland Scenic Railroad




