Family-friendly vacation rentals in Cumberland

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Top-rated family-friendly rentals in Cumberland

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Cabin in Great Cacapon

4.94 out of 5 average rating, 127 reviews

Cozy Cabin on the Cacapon River

The Cozy Cabin is set back off the Cacapon River banks with spectacular year round views. The property sits on 5 wooded acres with over 500 feet of river frontage and PRIVATE RIVER ACCESS. Bring canoes, kayaks and your fishing pole in the summer or in the winter light a fire and cozy up indoors. The spring brings abundant wildflowers and its the perfect location to view the fall foliage. We invite you to enjoy our city escape in the mountains. Fiber internet is now installed 500 mps internet

Aug 11 – 18

G$29,817 GYD per night

Guest favorite

Home in Cumberland

4.94 out of 5 average rating, 211 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.

Apr 18 – 25

G$21,574 GYD per night

Guest favorite

Cabin in Great Cacapon

4.92 out of 5 average rating, 241 reviews

Rustic Cabin on Cacapon River for Private Getaway

Rustic, 100+ year old primitive mountain cabin in West Virginia along the Cacapon River. Beautifully restored with wood stove, loft, & screened in porch. Access to 214 acres of private mountain land & over 1/4 mile of river frontage plus 1/2 acre pond, trails, and private shooting range. This cabin is 1-room and completely off grid. It has NO electricity or plumbing/running water, but does have a Porta-John serviced weekly. Renter will be cabin camping so pack accordingly; tents also welcome.

Jan 4 – 11

G$22,367 GYD per night

Guest favorite

Cabin in Frostburg

4.92 out of 5 average rating, 133 reviews

Big Savage Guest Cabin

Nestled on 10 acres near the summit of Big Savage Mountain is our home site which includes our guest cabin. Warm summer days and cool evenings make for a great vacation spot. In the country but just 1 mile from down town. Your retreat is just 3 minutes from dining, biking, hiking, swimming, and live music. Fall brings beautiful foliage and winter plenty of snow. There is something for fans of all seasons. We are only 5 minutes from Frostburg State University & 30 minutes from Deep Creek Lake.

Sep 1 – 8

G$24,626 GYD per night

Guest favorite

Cabin in Berkeley Springs

4.83 out of 5 average rating, 180 reviews

Retriever’s Retreat ~ High-Tech Log Cabin Oasis

Relax at the gorgeous 3BR 2Bath log cabin nestled in the mesmerizing forest setting of Berkeley Springs, WV. Recently renovated to bring in more outdoor light and modernize the cabin, its fantastic location just a few minutes from the booming Cacapon Resort State Park offers a perfect escape from the everyday hustle and bustle Stylish design and a rich list of high-tech amenities ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Basement Entertainment ✔ Sunny Deck ✔ Backyard ✔ High-Speed Wi-Fi

Sep 10 – 17

G$33,192 GYD per night

Guest favorite

Home in Cumberland

4.83 out of 5 average rating, 144 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 jacuzzi tub and seven-head shower. The house maintains its historic charm with exposed brick and has a balcony, back patio, and yard space.

Jun 13 – 20

G$22,000 GYD per night

Guest favorite

Home in Frostburg

4.93 out of 5 average rating, 206 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.

Aug 8 – 15

G$24,490 GYD per night

Guest favorite

Home in Cumberland

4.9 out of 5 average rating, 462 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.

Feb 16 – 23

G$30,300 GYD per night

Guest favorite

Cabin in Berkeley Springs

4.93 out of 5 average rating, 469 reviews

Horizon Hill-Log Cabin w/Hot Tub & Views!

Horizon Hill is a beautiful log home in Berkeley Springs, WV. Less than 2 hours from DC & Baltimore. Great for couples, families, and groups. Large three level deck with hot tub to enjoy the amazing mountain views. Warm up to next to the fire place at night. Nicely decorated and equipped with super fast Starlink Wi-Fi, Netflix, Amazon Prime & fully stocked kitchen for cooking. Only 2 minutes to Cacapon State Park and 15 minutes (easy drive) to Berkeley Springs. Dogs welcome!

Jan 19 – 26

G$49,327 GYD per night

Guest favorite

Home in Frostburg

4.86 out of 5 average rating, 255 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.

Dec 10 – 17

G$14,477 GYD per night

Superhost

Cabin in Capon Bridge

4.78 out of 5 average rating, 314 reviews

WV Mountain cabin

Beautiful cabin with perfect mountain views and private setting. This is a great cabin for reconnecting with your friends and family or a romantic getaway. The cabin is located on 5 acres of woods for you to explore.Has parking for up to 3 vehicles. A 4-wheel (SUV, pickup Truck) is required in winter months & in snow for access to this mountain ridge cabin! Sparkling clean, well maintained space. Maximum 5 guests, 2 queen beds plus a futon. Dog friendly w pet fee.

Sep 18 – 25

G$28,529 GYD per night

Guest favorite

Chalet in Great Cacapon

4.94 out of 5 average rating, 374 reviews

Fern Haven - Waterfront Chalet w/ WiFi & Hot tub!

Fern Haven is large waterfront home with space for the entire family! This home boasts 3 bedrooms and 3 baths with plenty of space outside for additional friends and family. Enjoy the sound of the river as you relax on the deck! Just 2 hours from DC, Baltimore and 2.5 hours from Philly and PBH. Bring your fishing poles, canoes, kayaks, or water wings and come enjoy this beautiful piece of West Virginia!

Dec 8 – 15

G$49,083 GYD per night