Cottage vacation rentals in Cumberland

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Top-rated cottage rentals in Cumberland

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Guest favorite

Cottage in Berkeley Springs

4.95 out of 5 average rating, 384 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.

Nov 24 – Dec 1

G$50,164 GYD per night

Guest favorite

Cottage in Hyndman

4.99 out of 5 average rating, 93 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 and wildlife 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. We also have central air!!

Oct 22 – 29

G$24,129 GYD per night

Guest favorite

Cottage in Winchester

4.97 out of 5 average rating, 425 reviews

Emma's Stone Cottage

Relax and unwind in the privacy of this wonderful stone cottage, which sits on 15 beautiful acres. In addition, it is located only 2.5 miles from I-81 and 14 minutes from Winchester Medical Center, Old Town Winchester, Shenandoah University and much more. Our cottage is fully furnished with all the comforts of home. From the full kitchen, central air, water softener, HD smart televisions, Wifi, outdoor firepit and more. It has everything you need for a peaceful and enjoyable stay.

Mar 10 – 17

G$25,639 GYD per night

Guest favorite

Cottage in Green Spring

4.98 out of 5 average rating, 66 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.

Aug 5 – 12

G$27,473 GYD per night

Guest favorite

Cottage in Cumberland

4.99 out of 5 average rating, 167 reviews

The Cottage on the Hill

Snuggled against a hillside, at the end of a small city lane, sits a charming private retreat. Park in your private space, walk down to a unique retreat high above the city and 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.

Aug 23 – 30

G$38,453 GYD per night

Guest favorite

Cottage in Flintstone

5.0 out of 5 average rating, 49 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.

Sep 20 – 27

G$34,598 GYD per night

Guest favorite

Cottage in Oakland

4.95 out of 5 average rating, 185 reviews

Pet-Friendly Cozy Home w/Hot Tub & Fire Pit

Wisp Away to this lovely cozy home. Located walking distance from Deep Creek Lake and only a short drive to Wisp Resort. Centrally located near all the area's amenities including parks, restaurants, golfing, boating, beaches and so much more. This home features a queen-sized bed, a full bathroom, and a kitchenette. Relax at home by the firepit or soaking in the hot tub. Pets are welcome. We look forward to sharing our cabin with you and your fur baby.

Sep 18 – 25

G$61,871 GYD per night

Guest favorite

Cottage in Oakland

4.93 out of 5 average rating, 60 reviews

Cheerful cottage 2 minutes from Deep Creek Lake

Just the right size and location for enjoying all Deep Creek Lake has to offer- including scenic hikes on many nearby trails, skiing at Wisp, or just enjoying time on the lake amongst bustling lake life. Then retreat back to our quaint cottage and enjoy time together. You will love our place because of its coziness, location, cleanliness, affordability and perfect size for a single family stay. *bathroom is in the bedroom *we have parking for a boat*

Aug 14 – 21

G$27,594 GYD per night

Guest favorite

Cottage in Oakland

4.98 out of 5 average rating, 100 reviews

Pet friendly-Cottage in the Woods

Tucked conveniently between Swallow Falls State Park and Deep Creek Lake, this recently renovated 2 bd cottage has everything you need for a weekend getaway or a much needed week(s) long vacation! Inside you will find a completely stocked kitchen, open living/dining area, full size bathroom, 2 bedrooms and a cozy nook with sleeper sofa and desk. Relax and unwind in the spacious backyard or charming balcony. *pets stay free

Dec 30 – Jan 6

G$33,696 GYD per night

Guest favorite

Cottage in Swanton

4.92 out of 5 average rating, 201 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.

Apr 23 – 30

G$54,146 GYD per night

Guest favorite

Cottage in Capon Bridge

4.97 out of 5 average rating, 150 reviews

The 3R's River, Relaxation, Retreat

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.

Feb 7 – 14

G$33,381 GYD per night

Guest favorite

Cottage in McHenry

4.97 out of 5 average rating, 111 reviews

Cozy getaway w/ Theater, Hot Tub, and Scenic Views

Nestled among the rolling hills of rural Garret County, Rest Assured provides you with a true country get-away, great for a romantic weekend, or a small family vacation. While only less than two miles from the Wisp resort and deep creek lake, you will find a feeling of seclusion and privacy.

Aug 17 – 24

G$36,538 GYD per night