Cottage holiday rentals in Cumberland

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Top-rated cottage rentals in Cumberland

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Guest favourite
A spacious wooden deck features a round table surrounded by six metal chairs. In the background, a serene pond reflects the sky, framed by lush greenery and trees, creating a calming outdoor setting.
Cottage in Meyersdale
4.92 out of 5 average rating, 49 reviews

Country farmhouse with 50 acres and private pond

Escape city life to this peaceful and relaxing country farmhouse on 50 hike able acres with spring fed pond for paddling, fishing and swimming. In the evenings, relax by the fire pit or on the deck while the kids catch fireflies, play games or watch a movie. You’ll feel a million miles from your hectic everyday life, yet it’s only 10-15 minutes to pick up groceries or head out for dinner at The Hen House or Cornucopia. Note: Hiking 50 acres not allowed during hunting season which starts 10/1.

Superhost
A cozy bedroom features a metal bed frame adorned with decorative pillows. A bedside lamp provides soft lighting, and blue floral wall art adds color. Light filters through the large window, which is framed by floor-length curtains.
Cottage in Berkeley Springs
4.75 out of 5 average rating, 68 reviews

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.

Guest favourite
The exterior of a charming brown cottage is surrounded by lush green foliage. A spacious wooden deck with railing leads to the entrance, which is framed by white French doors. A red shade sail is positioned above the deck, adding a pop of color.
Cottage in Berkeley Springs
4.95 out of 5 average rating, 465 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
A rustic cabin with mint green exterior is surrounded by trees, showcasing a wrap-around deck with wooden railings. The front entrance features a double door, and a grill is visible on the deck. A landscaped area with gravel complements the natural surroundings.
Cottage in Gerrardstown
5 out of 5 average rating, 18 reviews

Woodsy-Fire Pit-Scenic-Wraparound Deck-Play Room

Explore nature from this rustic cozy cabin in the mountains of WV. Everything has been renovated. Great secluded location yet close to restaurants, shopping, hiking, etc. While there are neighbors, you will feel secluded with trees all around. Located just 2 hrs from DC, 40 minutes from Harpers Ferry, 30 minutes to Winchester, 30 minutes to Charles Town Casino and racing, and 20 minutes to Martinsburg. There is also access to Back Creek at the end of the street just 0.4 miles away.

Top guest favourite
A blue cottage is illuminated at night, showcasing distinct architectural features including gabled roofs and decorative trim. The background reveals a sprawling view of the city lights, creating a contrast against the dark sky. Trees and greenery frame the scene, enhancing the serene atmosphere.
Cottage in Cumberland
4.99 out of 5 average rating, 192 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
The cottage exterior features a light-colored facade complemented by dark trim. A flag gently waves in the breeze, and surrounding lush greenery contributes to the tranquil setting. A gravel pathway leads to the entrance, creating an inviting access point.
Cottage in Hyndman
4.99 out of 5 average rating, 116 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
The cottage is nestled among vibrant autumn foliage along the riverfront. A rock cliff rises behind it, while a winding path leads to the house, which is surrounded by a mix of colorful trees. The serene river can be seen nearby.
Cottage in Green Spring
4.98 out of 5 average rating, 110 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.

Top guest favourite
An open-concept living area features wooden ceilings and stylish decor. A cozy sofa and coffee table are positioned on a patterned rug. A dining area with a round table sits adjacent to a fully equipped kitchen, which includes modern appliances and seating at the counter.
Cottage in Oldtown
5 out of 5 average rating, 63 reviews

* Sierra Farmstead *

Our cozy Cottage is located just minutes from the C&O Canal Towpath, the Potomac River and Warrior Mountain, 11 miles from Cumberland, MD and 12 miles from the Pawpaw tunnel. Enjoy all the country has to offer nearby including kayaking, fishing, hiking, biking, or stay on the farm and enjoy a fire in the yard with sunset views over the mountains. If you prefer to stay inside, the apartment has high speed Wi-Fi and TV with Amazon Video, Netflix, Hulu and more available.

Top guest favourite
A hot tub is situated on a wooden deck, surrounded by vibrant autumn foliage. Two glasses of amber-colored beverage rest on the edge of the hot tub, inviting relaxation while enjoying the natural scenery.
Cottage in Capon Bridge
5 out of 5 average rating, 62 reviews

*Fall* River Front Retreat *HotTub-FirePit-Kayaks*

Chase the fall colors in Capon Bridge, West Virginia. *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.

Guest favourite
A spacious blue house with a stone foundation is set against a backdrop of rolling hills. The structure features multiple windows and a chimney, while a covered patio extends from one side, offering outdoor seating options. Green grass surrounds the home.
Cottage in Flintstone
4.92 out of 5 average rating, 88 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.

Top guest favourite
Cottage in Berkeley Springs
4.95 out of 5 average rating, 189 reviews

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**

Guest favourite
A lakefront cottage is framed by lush green grass and trees, featuring a red metal roof and stone accents. A patio door leads to the serene outdoor space, with the calm lake visible in the background, providing a peaceful and inviting setting.
Cottage in Swanton
4.92 out of 5 average rating, 37 reviews

Lakefront Cottage with Spectacular Views

Lakefront cottage with tremendous views and private dock . Home is on a quiet lane with pedestrian friendly activity. This is an original lakefront cottage that has been completely updated. Swim or fish from the dock or shoreline, bring your own boat, or use the two sea kayaks provided. Well equipped kitchen. Quaint, updated cabin offers relaxing atmosphere, serene family environment. No large groups or partiers allowed.

Popular amenities for cottage rentals in Cumberland

Quick stats about cottage rentals in Cumberland

  • Nightly prices starting at

    Cumberland holiday rentals start at £121 per night before taxes and fees

  • Verified guest reviews

    Over 260 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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