
Cottage holiday rentals in Cumberland
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Nightly prices starting at
Cumberland holiday rentals start at $242 AUD per night before taxes and fees

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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!
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...

Guest Cottage on Historic Estate & Cattle Farm
Fully restored c.1900 farm house on 190 acre estate, ~1 hr from D.C. Cottage is situated at end of a farm road (past the main house and barns), very private w/ creek and cows right outside. Enjoy walks on the farm, local hikes, breweries & wineries, pick-your-own fruit farms, tubing on the Shenandoah, restaurants, antique shops, and more. 1 queen bdrm and bath on 1st flr, 2nd queen bdrm & loft with twin beds on 2nd flr. wifi, fire pit, small grill. Over 25 only, Max 4 adults. 1 SMALL DOG ONLY.

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.

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.

Cozy Ohiopyle/Fallingwater Cabin Hot Tub Fire Pit
OHIOPYLE< SEVEN SPRINGS<FALLINGWATER<STATE GAME LANDS*** Ski, Bike, Hike, Sled, Hunt, Fish -1.5 miles to OHIOPYLE , 20 minutes to SEVEN SPRINGS!!!! Perfect for a couples retreat or weekend with friends. Cute and cozy for a fun getaway. Outdoor fire pit. Fully equipped kitchen. Location>Location>Location!! Winter specials available! Linens and towels provided. 5 minutes to Fallingwater 2 minutes to rafting, hiking and biking
Popular amenities for Cumberland cottage rentals
Cottage rentals with a hot tub

Potomac River Retreat

Play & Stay near State Parks & Seven Springs

The Rustic Cottage

Cottage at Lost River Ridge

Pets? YES! Hot Tub | Fast Wi-Fi | Fire Pit

Cozy Home w/ Theater, Hot Tub, Mtn Views

Sunset View: Lakefront Pet-Friendly | Dock

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

Cottage on Chipmunk Alley in Davis

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

Brookside Cottage

Hawks Nest Stay

Cabin in the woods

Purple Kangaroo Cottages

Top-Rated 1891 Country Farmhouse + Game Room

Margaret’s Meadow
Private cottage rentals

Blue – Peaceful lakefront with a view

Laurel Highlands Cheerful 3 BR Creekside Cottage

Avery Pines Cottage

Lakefront Cottage with Spectacular Views

Riverfront Cottage with a large enclosed porch!

Milton Valley Cottage on Historic Estate Farm

House/cottage 2bed, Private yard, walk to Oldtown

Wooded Cottage Escape • Firepit • Near Bedford
Destinations to explore
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- House rentals Cumberland
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- Cottage rentals Maryland
- Cottage rentals United States
- Fallingwater
- Wisp Resort
- Seven Springs Mountain Resort
- Ohiopyle State Park
- Berkeley Springs State Park
- Cacapon Resort State Park
- Rock Gap State Park
- Whitetail Resort
- Deep Creek Lake State Park
- Swallow Falls State Park
- Blue Knob All Seasons Resort
- Laurel Hill State Park
- Green Ridge State Forest
- Fort Ligonier
- Laurel Ridge State Park
- Fort Necessity National Battlefield
- Shawnee State Park
- Old Town Winchester Walking Mall
- Laurel Mountain Ski Resort
- Museum of the Shenandoah Valley
- Lodestone Golf Course
- Linn Run State Park
- Western Maryland Scenic Railroad





