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

Guest suite in Shepherdstown

4.95 out of 5 average rating, 568 reviews

Historic Scrabble, Shepherdstown

The perfect private guest cottage situated beside a beautiful historic home in the unique community of Scrabble Unincorporated just a half-mile from the Potomac River. Modern, comfortable and tastefully decorated with full amenities and parklike surroundings with an abundance of nature at your doorstep. Close to Shepherdstown / Shepherd Univeristy (12 minutes), Martinsburg (20 minutes), Harpers Ferry (20 minutes) and in the heart of civil war history including the famed Antietam National Park.

Sep 9 – 16

R1,564 ZAR 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.

Feb 18 – 25

R1,916 ZAR 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.

Dec 6 – 13

R1,987 ZAR 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 30 – Oct 7

R2,185 ZAR 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.

Jul 14 – 21

R1,974 ZAR 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.

Nov 15 – 22

R2,175 ZAR 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.

Sep 30 – Oct 7

R2,277 ZAR 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.

Apr 6 – 13

R2,697 ZAR per night

Guest favorite

Home in Frostburg

4.86 out of 5 average rating, 254 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.

Feb 4 – 11

R1,237 ZAR 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.

Oct 10 – 17

R2,566 ZAR per night

Guest favorite

Cabin in Deep Creek

4.98 out of 5 average rating, 105 reviews

Boulder Ridge Cabin, close to Deep Creek, Maryland

Boulder Ridge Cabin is surrounded by woods, but within 15 minutes of Deep Creek Lake, swimming, boating, hiking, shopping, restaurants, Wisp Resort with skiing, snowboarding, mountain coaster, whitewater rafting at Adventure Sports Center International, rock climbing, hiking. Swallow Falls State Park and Herrington Manor State Park are about 15 minutes drive. Piney Mountain State Forest is within walking distance. Mountain biking and fishing are also close by.

Oct 24 – 31

R2,505 ZAR per night

Guest favorite

Cabin in Champion

4.92 out of 5 average rating, 560 reviews

Cabin in the Woods Seven Springs

Newly renovated home on a private wooded lot-just 5 mi from Seven Springs Resort and 16 mi from Falling Water and Ohiopyle. Well equipped! Sleeps 6 comfortably (3bdrm/1.5 bath)! Relax & Enjoy the Mountains! ***We have recently replaced a couch and chair and some bedding that photos don’t reflect. We are scheduling new photo shoot and plan a remodel on 2024! If you want to see updates photos let me know and I’ll send some less professional ones!

Sep 27 – Oct 4

R3,083 ZAR per night