Family-friendly holiday rentals in Allegany County

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.

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.

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.

Steeple View Flat in Historic District

Relax in your first level flat. Entire private efficiency suite with a secure self check in. The entrance located along side of the main house in Cumberland’s Historic District. You can safely park your car and walk to many of Cumberlands amenities. If you’re biking, they can be stored inside. Canal Place has unique shops a winery and a bike rental facility. Cumberland theater is adjacent to the property, also Baltimore St. Promenade offers a delicious choice of indoor and outdoor dining.

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.

Easygoing

Tired of the chaos and need a place to unwind and relax ? We have the perfect place for you! A quaint, quiet cabin to let you clear your mind and spirit after a day of hiking, biking or kayaking since we are only five miles from both the Paw Paw tunnel and the Potomac river. The cabin is equipped with electric, heating, stove top, microwave, large deck, hammock chairs, horseshoe pit, 2 double size futons with room to spare, indoor toilet but BEST of all is showering outside!

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.

Hilltop Cabin Retreat - Secluded & cozy - Wi-Fi!

The Sonny Side Hilltop 10-acre Cabin is the perfect secluded getaway to unwind and enjoy nature. Spend quality time with friends/family, explore the outdoors, ATV trails, or hunt with appropriate tags - contact for more details. My father (Sonny) built this cabin in 2004 with his own two hands. It was his primary residence until passing from cancer at my sister's home in Maryland in 2019. We would like to share this lovely cabin with guests to help offset costs. Please Enjoy!

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.

The Shadoe on Greene

Just a stones-throw from everything Cumberland has to offer, The Shadoe on Greene is at the heart of it all. Literal steps from the Western Maryland Scenic Railroad, the Great Allegheny Passage trail & the Historic City Center, with a wide array of local shops and eateries. This unique property was built in the 1850's and has been lovingly restored to embrace it's history, as well as provide all of the modern amenities you'd expect.

Piney Mtn House

Become part of Mountain Maryland discovering your next cozy escape in the newly renovated modern bungalow. The Appalachian range will tuck you in the small town of Eckhart, closely boarding Frostburg, with all its unique attractions, entertainment, hiking trails, and state parks. No body does small town like local Frostburg. And there is no better way to unwind than to make the Piney Mountain House your home away from home.

Evergreen Escape | Hot Tub, Sauna, King Bed & Pets

Welcome to our spacious 4-bed, 2-bath house in serene Great Cacapon, near Berkeley Springs, WV! Enjoy modern amenities, including a hot tub for post-adventure relaxation, along with being dog-friendly. Nestled in a secluded area, our property offers privacy and tranquility for a peaceful retreat. NO CELL PHONE SERVICE, WIFI CALLING ONCE ONSITE AND LANDLINE! STRONG WIFI CONNECTION