
Cottage holiday rentals in Cumberland
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Top-rated cottage rentals in Cumberland
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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.

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.

Hawks Nest Stay
Welcome to the Hawks Nest! Nestled in the beautiful Laurel Highlands ,Confluence, PA, "where rivers meet mountains", this new retreat offers a perfect blend of rustic charm & modern amenities! An ideal getaway for outdoor enthusiasts & -Attractions: Confluence/GAP Bike trail-4.7 Miles, Youghiogheny River Lake-4.7 miles, Marina-7.8 miles, Mount Davis-15 miles, Ohiopyle State Park-15miles, Fallingwater-9.6 miles, Seven Springs Resort-20 miles, Laurel Caverns & Deep Creek Lake, MD-32 miles.

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.

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.

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) Come step into nature and nurture your spirit at our riverfront haven.

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.
Popular amenities for Cumberland cottage rentals
Cottage rentals with a hot tub

Wide Open Spaces - 4 Bedroom Cottage

Sunset View: Lakefront Pet-Friendly | Dock

Just Chillin' - 4 Bedroom Cottage

Almost Heaven - 4 Bedroom Cottage

2BR Spacious House w/private hot tub

Vital Idyll - 4 Bedroom Accessible Cottage

Changes in Altitude - 4 Bedroom Cottage
Pet-friendly cottage rentals

Sky Valley Lake access home/Quiet Cozy

Country farmhouse with 50 acres and private pond

Secluded Mountain Top Retreat | Stunning Views

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!!

Mountain Oasis Cottage
Quick stats about cottage rentals in Cumberland

Nightly prices starting at
Cumberland holiday rentals start at $235 AUD 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!
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- 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
- Swallow Falls State Park
- Laurel Hill State Park
- Museum of the Shenandoah Valley
- Deep Creek Lake State Park
- Fort Ligonier
- Old Town Winchester Walking Mall
- Fort Necessity National Battlefield
- Laurel Ridge State Park





