Holiday rentals in Pinto

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.

Value · Family · TV

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.

Location · Value · Getting around

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.

Location · Value · Nearby

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.

Value · Location · Walkability

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.

Family · Location · Access

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.

Value · Family · Hiking

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.

Location · Family · Hiking

Mountain view Grand 6BR in LaVale |15min Rocky Gap

Escape to this gorgeous, spacious 6-bedroom, 3-bath retreat in the heart of LaVale, MD! Perfect for families, friend getaways, or team retreats, this charming haven offers cozy comfort, stylish charm, and unbeatable convenience. Nestled on scenic National Highway, you're just minutes from historic Cumberland, the scenic railroad, majestic Rocky Gap, the "bluest water in the state" Lake Habeeb, rugged Wills Mountain, and the serene beauty of Deep Creek Lake.

Location · Family · Hospitality

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.

Family · Location · Hospitality

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.

Family · Value · Hiking

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.

Location · Value · Cleanliness

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.

Value · Location · Parking