Cottage holiday 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.

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Guest favourite
Cottage in Berkeley Springs
4.95 out of 5 average rating, 494 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.

Top Guest favourite
Cottage in Confluence
4.96 out of 5 average rating, 80 reviews

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.

Top Guest favourite
A charming cottage sits atop a hillside, with a sloped pathway leading down surrounded by stone steps and bordered by a white privacy fence. The surrounding area features colorful autumn foliage and offers a peaceful view of the landscape below.
Cottage in Cumberland
4.99 out of 5 average rating, 201 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.

Top Guest favourite
A serene pond is situated beside the cottage, featuring a gentle fountain that adds a calming touch. A wooden deck with a white bench overlooks the water, surrounded by trees displaying autumn foliage. Fallen leaves create a natural pattern on the pond's surface.
Cottage in Hyndman
4.99 out of 5 average rating, 120 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.

Top Guest favourite
Cottage in Green Spring
4.98 out of 5 average rating, 118 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.

Guest favourite
Cottage in Flintstone
4.93 out of 5 average rating, 95 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.

Guest favourite
A hot tub bubbles invitingly on a wooden deck surrounded by trees. An outdoor dining set, including a table and four chairs, is positioned nearby alongside a gas grill, creating an ideal space for relaxation and entertaining.
Cottage in Swanton
4.92 out of 5 average rating, 282 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

Top Guest favourite
Two black rocking chairs are positioned on a stone patio, each adorned with a decorative pillow. A wide window provides views into the interior, framed by a white picket fence in the background, enhancing the outdoor sitting area.
Cottage in Oakland
4.96 out of 5 average rating, 196 reviews

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.

Guest favourite
Cottage in Oakland
4.89 out of 5 average rating, 237 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

Top Guest favourite
A charming stone cottage is visible through a canopy of autumn leaves, surrounded by a mix of greenery and trees. A pathway leads to the cottage's entrance, which features a covered porch. The natural setting provides a sense of seclusion and tranquility.
Cottage in Winchester
4.98 out of 5 average rating, 562 reviews

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.

Top Guest favourite
A serene mountaintop cottage is surrounded by lush greenery, featuring rustic wooden siding. The spacious deck offers outdoor seating, while steps lead to a well-maintained lawn. Natural light filters through the trees, creating a peaceful atmosphere in the inviting landscape.
Cottage in McConnellsburg
4.98 out of 5 average rating, 124 reviews

BedrockCottage-CowansGap/GoldfishBarn/Merc Academy

Bedrock Cottage is a cozy mountaintop home-away-from-home surrounded by nature. The cottage sits on 2 wooded acres just 4 miles from JLG, 11 miles from Mercersburg Academy, and 6 miles from Cowan's Gap State Park. Fishing, swimming, kayaking, paddle-boats, picnicking, hiking and more are available at the Park. We are also just 6 miles from the Goldfish Barn Event Center and 18 miles from Whitetail Ski Resort

Top Guest favourite
A hot tub is positioned under a covered porch, featuring bubbling water and a soothing green light. In the background, the tranquil Cacapon River is visible, surrounded by autumn foliage. A fire pit can be seen nearby, contributing to the relaxing outdoor ambiance.
Cottage in Capon Bridge
4.97 out of 5 average rating, 221 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.

Popular amenities for Cumberland cottage rentals

Quick stats about cottage rentals in Cumberland

  • Nightly prices starting at

    Cumberland holiday rentals start at $289 NZD 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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