
Holiday rentals in Pinto
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Top-rated holiday rentals in Pinto
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Rails and Trails Retreat ~ historic home w. yard
Spacious, beautifully restored historic home in a prime Cumberland location perfect for families, couples, and groups exploring Western Maryland. Just 100 feet from the GAP and C&O Canal trails, and an easy walk to downtown historic Cumberland with restaurants, cafés, shops, and the train station. The home blends historic charm with modern comfort, offering generous living space across three levels, a fully equipped kitchen, and a large private backyard - a peaceful retreat after a full day out.
4.94 out of 5 average rating, 169 reviews
CJ’s Escape Great location & just like home
Make yourself at home! Located 10 minutes from Frostburg, close to Cumberland, and a 45 min ride to Deep Creek! Right off I-68 and close to all the necessities but tucked away on a small and quiet street. Enjoy the flat backyard with a fire pit and seating for 6. Fully stocked kitchen, smart tv, and a quiet neighborhood that’s close to all the conveniences. Enjoy the local history, visit state parks, and the many breweries in the area. No smoking of any kind, no guests, and no parties please.
5.0 out of 5 average rating, 56 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.
4.99 out of 5 average rating, 161 reviews
The Woodland Getaway
The beautiful Woodland Getaway is tucked away from everyday hustle and bustle. Stretch out on a lounge chair & watch the wildlife on the elevated screened in porch surrounded on three sides by trees. Sit on the ground level back deck at dusk & wait for the deer to arrive. Secluded and private the Woodland Getaway is the perfect spot for rest and relaxation. Come enjoy the view of wildlife and sunsets through our beautiful bay windows and enjoy the quietness and serenity of mother nature.
4.91 out of 5 average rating, 108 reviews
Martha’s Cabin
Mountain Maryland's private cabin retreat is a completely renovated 1 bedroom, 1 bathroom getaway perfect for up to two guests. The peaceful wooded surroundings with walking paths to the property's creek will bring you relaxation and peace. Only minutes from Frostburg's small town attractions, Frostburg State University campus, downtown entertainment, shopping, local area hiking trails and state parks! Martha's Cabin is a perfectly tucked away yet with everything you need nearby.
4.95 out of 5 average rating, 118 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.
4.92 out of 5 average rating, 160 reviews
THE STUDIO
A wonderful 2 bedroom home on the west side of Cumberland in a small area of Cresaptown. Less than 8 miles to Cumberland..Completely remodeled with a great kitchen, a deck, hotub and a porch off the Master bedroom. Walk in shower bathroom right off the living room with a powder room and laundry off the Master bedroom. Very close to downtown historic Cumberland, C & O Canal, Potomac River and Frostburg State College. Also close the the Allegany Fair Grounds.
4.83 out of 5 average rating, 63 reviews
The Hidden Tree
Nestled in the heart of Cumberland. Our cozy home offers a perfect blend of comfort and convenience for your stay. Whether you're here for business or leisure, we've got you covered! Conveniently located near UPMC Hospital, Planet fitness, Downtown Cumberland, Rocky Gap Casino and much more! Explore the vibrant neighborhood or venture out to discover the hidden gems of Cumberland. Book your stay at “The Hidden Tree” today and make unforgettable memories.
4.92 out of 5 average rating, 103 reviews
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.
4.94 out of 5 average rating, 287 reviews
Sweet 68
This stylish and unique place sets the stage for a memorable trip. You will feel right at home in this studio equipped with all the conveniences of home. Studio is in own private space with own entrance where you can sip some coffee on either of the patios. It is also located steps away from the hot tub. This studio apartment is located 1 mile off interstate 68. It is convenient to local restaurants in walking distance.
4.92 out of 5 average rating, 112 reviews
Allegany Retreat
This 1800s Duplex home has tons of charm & comfort! Close to Main street n shops 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 in consideration of future guests We love animals but unfortunately they are not generally allowed. Exterior cameras for everyones security.
4.83 out of 5 average rating, 228 reviews
Corner Tavern-Allegheny Suite
Nestled above Corner Tavern & Cafe in historic downtown, this newly renovated modern apartment supplies you with all the comforts of home in a tasteful design. Our location provides all the benefits of a night out of town, located in historic downtown, above a tavern & cafe, you'll find food, drink & maybe even music in a few short steps from your apartment.
4.99 out of 5 average rating, 101 reviewsPopular amenities for Pinto holiday rentals
Other great holiday rentals in Pinto

Mountain view Grand 6BR in LaVale |15min Rocky Gap
5.0 out of 5 average rating, 35 reviews
Milnor Crossing
4.92 out of 5 average rating, 12 reviews
The Jackson House / Walk to FSU
4.6 out of 5 average rating, 5 reviews
Bobby Joes Cozy Little Cabin, LLC
4.94 out of 5 average rating, 80 reviews
616 Mountain Suite
4.96 out of 5 average rating, 51 reviews
WiggerZen
5.0 out of 5 average rating, 82 reviews
Mountain Maryland Getaway
4.93 out of 5 average rating, 59 reviews
The Whistle Stop in Cumberland, Maryland
4.78 out of 5 average rating, 9 reviewsDestinations to explore
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- Fallingwater
- Seven Springs Mountain Resort
- Wisp Resort
- Timberline Mountain
- Ohiopyle State Park
- Berkeley Springs State Park
- Blackwater Falls State Park
- Rock Gap State Park
- Swallow Falls State Park
- White Grass
- Cacapon Resort State Park
- Deep Creek Lake State Park
- Laurel Hill State Park
- Green Ridge State Forest
- Fort Necessity National Battlefield
- Old Town Winchester Walking Mall
- Laurel Ridge State Park
- Museum of the Shenandoah Valley
- Whitetail Resort
- Linn Run State Park
- Laurel Mountain Ski Resort
- Shawnee State Park
- Lodestone Golf Course
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