House vacation rentals in Cumberland

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Top-rated house rentals in Cumberland

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Top guest favourite
A well-equipped kitchen features wooden cabinetry and an island with seating for four. Natural light fills the space, highlighting the polished wood floors. A full-size refrigerator, stove, and microwave are visible, along with counter appliances and a window offering an outdoor view.
Home in Markleton
4.93 out of 5 average rating, 107 reviews

The Country Ranch

Nestled in the Laurel Highlands on 3 acres of private ground with surrounding farmland. Peaceful & private, this property offers a large backyard with amazing sunset views & starlit night skies. This vacation home is 3 miles from the Markleton GAP trailhead and 10 miles from Youghiogheny Lake. Other nearby attractions include Mt Davis (the highest point in PA), High Point Lake, Ohiopyle, Falling Water, Kentuck Knob, Seven Springs & Hidden Valley Ski Resorts, and Laurel Hill & Kooser State Parks.

Guest favourite
A Cape Cod style cottage is depicted, featuring a porch with a sloped roof and a welcoming entrance. The surrounding yard is green, bordered by neatly trimmed shrubs. In the background, rolling hills are visible, providing a natural setting.
Home in Cumberland
4.93 out of 5 average rating, 273 reviews

Jacob's Cottage

Free WI-FI now available. Our place is good for couples, solo adventurers, business travelers and families (with kids). The Cottage is a quaint, Cape Cod style house built in 1950. It sits high on a hill in the heart of Maryland's Appalachian Mountains in Allegany County. It is surrounded by views of Wills Mountain and Shrivers Ridge. The Cottage sits amongst a 660 acre family managed forest. Visitors have spotted deer, turkey, rabbits, squirrels, black bear and a multitude of song birds.

Top guest favourite
The ranch house is highlighted by a vibrant red roof, set against a backdrop of lush greenery. Large windows provide ample natural light, and a spacious patio with seating areas invites relaxation. The surrounding lawn is well-manicured, enhancing the property’s peaceful setting.
Home in Hyndman
4.99 out of 5 average rating, 158 reviews

Wills Mountain Ranch

Lovely, private home overlooking our beautiful valley with breathtaking views of Wills Mountain. It is the perfect setting for a family retreat/reunion. The ranch house has a red roof in the pictures. My husband & I live in the 3 story. We have a in-ground pool on property (heated from Mid-May to early September), a gas grill, and fire pit on the large scenic patio for your enjoyment. The large windows & patio offer a spectacular view of Wills Mt. The ranch house offers a quiet getaway retreat.

Top guest favourite
Home in Cumberland
5 out of 5 average rating, 126 reviews

NEW LISTING-"Cumberland Cottage"-charming,quaint

Relax in this charming, renovated rancher in a peaceful setting. Located outside of the city limits but convenient to attractions and dining. This home is comfy with all the amenities you have in your own home. Outside area for your children to play or for you to relax on the back porch. Cumberland is in easy driving distance to PA and WV. Enjoy cooking together and dining or playing games in the dining room, then relaxing in the living area. Renovated but still keeping the charm of a rancher.

Guest favourite
An aerial view captures the cottage nestled among vibrant autumn foliage, surrounded by colorful trees. The serene pond reflects the rich hues of fall, while solar panels are visible on the cottage roof. A winding dirt road leads to the property, enhancing the secluded atmosphere.
Home in Clearville
4.92 out of 5 average rating, 317 reviews

Grouseland's Pondside Vacation Cottage

Set about a quarter mile of the road, our pet friendly solar powered vacation cottage is a perfect getaway for anyone trying to spend some alone time with nature! Guests have complete privacy inside the cottage with a full kitchen, two TV's, Wi-Fi, and a mini split system for heating and cooling. As well as exclusive access to the hot tub, fire pit and pond outside! We also have various shared hiking trails through the woods surrounding the cottage for campers and cottage guests to enjoy!

Top guest favourite
The exterior entryway features a set of stairs leading to a porch with white railing and overhead lighting. A small bush is visible beside the stairs, and the brick faƧade of the home provides a warm appearance, enhanced by the nighttime ambiance.
Home in Cumberland
4.94 out of 5 average rating, 105 reviews

Great Location, Spacious, Comfy 2 bdrm 3 bed home

This home is centrally located near all things fun and exciting to do in Cumberland. Situated in a quiet residential neighborhood in the Western Maryland mountains. Minutes from historic downtown, the Potomac River, Rocky Gap State Park, Pennsylvania, the University of Pittsburg Medical Center, the C &O canal and much more. This home features 3 queen beds, 2 bedrooms both with 55" TV's and blackout curtains, a large separate dining room, a spacious kitchen, and living room with a 65" TV.

Top guest favourite
A charming two-story house is surrounded by well-tended gardens, featuring a gravel driveway leading up to the front porch. The exterior is painted in a soft gray hue, complemented by large windows that offer opportunities for natural light.
Home in Frostburg
4.94 out of 5 average rating, 234 reviews

Country Home Near Main St. & Trail

Welcome to this charming and cozy home sitting at the highest point in Frostburg. Incredible mountain and forest views from the upstairs windows, lots of old house details and including two staircases and a sleeping porch. There are hardwood floors throughout. Lots of space to relax. Two full baths, one with shower and one with tub/shower. Gas range and fully stocked kitchen. Smart TV's in two bedrooms, and in the main living room. Strong Wifi, and a washer and dryer in the basement.

Guest favourite
A corner view of the charming brick facade of the house is captured, featuring a white door adorned with glass panels. The rich pink color of the brick is complemented by green foliage overhead. A lantern is positioned beside the door, creating a welcoming entryway.
Home in Cumberland
4.84 out of 5 average rating, 167 reviews

Charming 1907 Home in Historic Downtown Cumberland

This charming 1907 home is located just blocks from the main pedestrian street in Historic Downtown Cumberland and a 10 minute walk from Canal Place, the C&O Canal Great Allegheny bike trails, and the Western Maryland Scenic Railroad. The remodeled interior is equipped with all the modern conveniences, including a large kitchen and bathroom with large tub and seven-head shower. The house maintains its historic charm with exposed brick and has a balcony, back patio, and yard space.

Top guest favourite
An exterior view of the farmhouse displays rustic wooden siding and a green metal roof. A small deck with a seating area sits at the entrance, surrounded by manicured grass and flower beds. Lush trees and shrubbery frame the property, enhancing its natural setting.
Home in Warfordsburg
4.96 out of 5 average rating, 190 reviews

Tall Spruce Farmstead in South Central PA

A quaint old farmhouse in the hills of Southern Fulton County, PA. Only 5 miles from Hancock, MD and 12 miles from Berkeley Springs, WV. There is a small deck, ideal for watching the deer and other wildlife. Close to the C&O Canal Rail Trail where you can enjoy walking or biking. Only 30 minutes from White Tail Ski Resort, Ft. Frederick, Rocky Gap Casino, Hagerstown and Cumberland. Come and enjoy the peace and quiet of country living in the newly renovated Tall Spruce Farmstead.

Guest favourite
A vibrant red window frame complements the natural light streaming through diamond-shaped panes. A potted plant sits on a wooden shelf beneath the window, alongside wooden signs that read 'WELCOME' and 'Make Some Memories.' A bicycle-themed artwork is displayed nearby.
Home in Cumberland
4.9 out of 5 average rating, 568 reviews

Cumberland Street House -GAP trail perfection!

Cyclists dream come true! The Cumberland Street House is less than a quarter mile from the Great Allegheny Passage - perfect for large groups! All of Cumberland's charm within walking distance. Downtown restaurants and shops only a half a mile away. Historic district, Cumberland Theatre & Western Maryland Scenic Railroad are just around the corner. Bikes can easily be stowed in the back room off the kitchen. Easy parking, and fenced-in yard is great for kids and pooches.

Guest favourite
A charming outdoor seating area features two intricately designed white wicker chairs with floral cushions and a small table. Soft string lights enhance the space, while a lush green view is visible in the background through the open area.
Home in Cumberland
4.91 out of 5 average rating, 137 reviews

Queen City Quarters- cozy, historic, 1920s home

Stay in a quiet setting as you explore Cumberland, MD. Enjoy a day trip on the nearby, scenic, steam train. Bike the Gap and C&O trail, minutes away. Explore the restored historic downtown with shopping and restaurants. This space is not suitable for small children or those with mobility concerns. No large groups or parties. Bedroom doors are louvered doors. See pictures. Research city and area if you are unfamiliar with economic conditions. We have a bike rack for 3 bikes.

Guest favourite
A modern kitchen features light gray cabinetry with an island centerpiece. Stainless steel appliances, including an oven and refrigerator, are complemented by a colorful bowl display. A detailed wall graphic provides helpful kitchen rules, while ample counter space offers convenience for meal preparation.
Home in Frostburg
4.87 out of 5 average rating, 326 reviews

Allegany Connection

NOTICE: extra santizing of hand touching areas in place for your protection. This eclectic 2-story duplex, late 18th century structure has both old and new charm. Single BR & bath upstairs; LR and Kit downstairs. Only 1 block from Main St. restaurants & unique shops. All are welcomed. Please bring your own infant bed. Sorry no pets. Free reserved parking for 1 vehicle & fast Wi-Fi. Instant booking is on. ABSOLUTELY NO SMOKING, or any kind is permitted inside our home.

Popular amenities for Cumberland house rentals

When is the best time to visit Cumberland?

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Avg. price$168Ā CAD$154Ā CAD$168Ā CAD$168Ā CAD$174Ā CAD$172Ā CAD$182Ā CAD$185Ā CAD$182Ā CAD$171Ā CAD$175Ā CAD$168Ā CAD
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Quick stats about house rentals in Cumberland

  • Total vacation rentals

    Explore 50 vacation rentals in Cumberland

  • Nightly prices starting at

    Cumberland vacation rentals start at $42Ā CAD per night before taxes and fees

  • Verified guest reviews

    Over 2,710 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    40 of Cumberland vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Cumberland rentals

  • 4.9 Average rating

    Cumberland stays are highly rated by guests—averaging 4.9 out of 5!

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