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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Top guest favorite

Cabin in Oakland

4.95 out of 5 average rating, 217 reviews

Private-Pool Access-Deck Fireplace & Hot Tub-XTRAS

Business Name: LAZY BEAR LODGE AT DEEP CREEK LAKE Need some quality time away but want to avoid crowds & still be close to everything at the Lake? Secluded, private and located on 3 acres in a serene forest of hemlock trees & boulders, this natural space is calming & architecturally pleasing to the eye and soul! Let your cares slip away with the smell of a real wood fire, rustic décor, warm color paints, stone and wood. HotTub by fireplace on deck. CARC membership, lots of firewood and supplies.

Guest favorite

Cabin in Great Cacapon

4.94 out of 5 average rating, 141 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

Guest favorite

Chalet in McHenry

4.83 out of 5 average rating, 193 reviews

Drake's Nest on Deep Creek Lake

This cedar chalet offers the best of both worlds. It is located on the water's edge (really) and offers spectacular views of the slopes at Wisp ®. Convenience stores, amusements and restaurants located a short walk away. Rental includes use of a pedal boat, swim inflatables, tow tubes and boat slip. Visitors during Spring and Autumn enjoy Swallow Falls/Muddy Creek Falls ( tallest in MD) 15 min drive. *Holiday weekends require a 3 night minimum. *Renters under 25 may be charged a damage deposit.

Superhost

Chalet in McHenry

4.85 out of 5 average rating, 188 reviews

R & R Retreat

20% Discounts on week rentals. Lakefront 2 level chalet in McHenry, Md. on Deep Creek Lake with dock and reserved boat slip. Across the lake from WISP ski resort. Ideal and easy access and swimming in the lake. Restaurants, amusements, shops, and more only a 100 yard walk from house. 3 BR + loft, sleeps 9. Fireplace, fully furnished kitchen, TV, WIFI, A/C in summer (window units), heat and much more. Minimum 3 night stay during the summer and holidays. Beautiful view of lake and mountain.

Guest favorite

Cabin in Berkeley Springs

4.84 out of 5 average rating, 202 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

Top guest favorite

Cabin in Oakland

4.86 out of 5 average rating, 136 reviews

Wooded camp w/lake views/fire pit. Great location.

Cozy lake view camp in Deep Creek. Centrally located to all amenities. Open floor layout with full kitchen. Master bedroom has a Queen bed, master BR, closet, and lake view via sliding doors leading to the deck. Second bedroom features bunk beds (weight limit 165lbs) and a computer desk. Lastly, the 3rd BR contains a Full bed. There's also separate laundry room. Back deck overlooks Deep Creek Lake. Large firepit. Wireless internet, ROKU TV's, DVD, Wii gaming and Google Chromecast provided.

Guest favorite

Apartment in Confluence

4.9 out of 5 average rating, 212 reviews

Turkeyfoot Wisteria Apartment

The Turkeyfoot Wisteria is a very convenient first floor apartment located on thel Confluence of the three rivers. The livingroom has two fold down sofas and a flat screen tv. The bedroom has a queen bed. There is a full kitchen and a full bathroom with a tub and shower. Each apartment has a private outdoor table and chairs so you can enjoy the beautiful view. We are very conveniently located to everything in town including the bike trail, and great fishing at your fingertips.

Superhost

Cabin in Swanton

4.79 out of 5 average rating, 92 reviews

"Whispering Pines"

Soft greens and powder blues adorn the interior and blend seamlessly with the lush natural setting of "Whispering Pines." The home is conveniently located within minutes of the State Park and could be the perfect place to gather for your next family vacation destination! You’ll love my place because of the views, the location, the ambiance, and the outdoors space. My place is good for couples, solo adventurers, business travelers, families (with kids), and furry friends (pets).

Superhost

Chalet in Oakland

4.91 out of 5 average rating, 128 reviews

Spectacular Chalet, Timroc II, close to lake, Wisp

ENJOY every season!! Short walk to the lake and dock! ! 15 minute drive to Ski Wisp! Fire pit, decks and screened in porch! Relax in the hot tub, enjoy family and/ or friends time and just get away from it all! 5 comfortable sized bdrms, each with large windows letting in natural daylight. First floor master, hardwood flooring throughout, many sliders for easy access. Finished bsmt with pool table, separate bdrm, full bath and laundry! DON'T SEE YOUR DATE, PLEASE CALL!

Superhost

Cabin in Champion

4.88 out of 5 average rating, 149 reviews

2 miles from 7 Springs-Borders State Park-Dogs OK!

Roomy 3 bedroom, 2 bath getaway situated on 3 acres abutting Laurel Hill State Park. Recently renovated with new flooring, paint, lighting and decor. Walk out the back door and walk directly into State Park. Perfect place to retreat for a long weekend or week in the mountains. Three minute drive from 7 Springs Resort, 15 minutes to Hidden Valley. Dogs welcome with pet fee!

Guest favorite

Home in Frostburg

4.83 out of 5 average rating, 185 reviews

Allegany Retreat

This 1800s Duplex home has tons of charm & comfort! Close to main street and all that it offers. Original wood floors. Snacks & coffee for your enjoyment. Close to GAP trail n fantastic scenic views. Please NO LOUD noises after 10pm. ABSOLUTELY NO SMOKING inside our home. NO animals allowed. Exterior cameras for security, front and back.

Guest favorite

Home in Confluence

4.91 out of 5 average rating, 221 reviews

Page Landing in Confluence

The house is close to the treasures of the Laurel Highlands. Top attractions are the Confluence rivers and Lake, Ohiopyle, Fallingwater, Seven Springs and Nemacolin Woodlands. You’ll love the place because of the ambiance of the house. The screened in porch is very relaxing after a day at the beach, on the lake or river or on the slopes.