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

Modern 3BR Farmhouse in the Country
Welcome to 1891 Farmhouse, your perfect country getaway, just outside of Winchester, VA. Experience the best of both worlds: historic charm thoughtfully blended with modern living and amenities. The well-appointed kitchen is ready for you to create wonderful meals. The Master Bedroom offers a peaceful retreat with a private en-suite bathroom featuring double sinks. For fun, head to the separate Game Room which features ping pong, pool, and an arcade game. Proud to be a Veteran-Owned Property.

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.

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.

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.

Cozy Cottage in the heart of Berkeley Springs WV
Welcome to Elizabeth Cottage in honor of our Queen HRH Elizabeth II. Our spacious 3 bedroom cottage will make you feel right at home in the historic town of Berkeley springs! We welcome all pets and have a fully fenced in yard and screened in porch for them to enjoy! We are walking distance from our small town shops, and restaurants! >British Cottage Style >55" TV w/ roku streambar >Xfiniti Wifi >Hot tub, Fire pit, Grill **Low Cleaning Fee**

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.

Avery Pines Cottage
Set apart on our five-acre property, this newly constructed cottage is nestled in a quiet spot—nicely separated from the main house, with trees providing a natural privacy buffer. 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.

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
Pet-friendly cottage rentals

Brookside Cottage

Country farmhouse with 50 acres and private pond

Cozy Cottage in the heart of Berkeley Springs WV

The River House

Hidden Hill - Cozy Downtown Cottage with Hot Tub!!

Modern 3BR Farmhouse in the Country

Quiet Cottage in the Woods

Mountain Oasis Cottage
Private cottage rentals

The Hillside Hideaway

Potomac River Retreat

Brookside Cottage

Cozy Cottage in the heart of Berkeley Springs WV

The Cottage on the Hill

The River House

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

Hidden Hill - Cozy Downtown Cottage with Hot Tub!!
Cottage rentals with a pool

Wide Open Spaces - 4 Bedroom Cottage

Just Chillin' - 4 Bedroom Cottage

Almost Heaven - 4 Bedroom Cottage

Vital Idyll - 4 Bedroom Accessible Cottage

Changes in Altitude - 4 Bedroom Cottage
Quick stats about cottage rentals in Cumberland

Nightly prices starting at
Cumberland vacation rentals start at G$33,472 GYD 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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- Wisp Resort
- Fallingwater
- Seven Springs Mountain Resort
- Whitetail Resort
- Berkeley Springs State Park
- Ohiopyle State Park
- Cacapon Resort State Park
- Blue Knob All Seasons Resort
- Rock Gap State Park
- Swallow Falls State Park
- Deep Creek Lake State Park
- Fort Ligonier
- Museum of the Shenandoah Valley
- Old Town Winchester Walking Mall
- Laurel Hill State Park
- Fort Necessity National Battlefield
- Green Ridge State Forest
- Laurel Ridge State Park




