Townhouse holiday rentals in Western Maryland

Roxy’s Retreat — pet friendly with hot tub!

Ready to unwind? This prime location Airbnb is the perfect place to escape with your friends and family — furry friends included! Just 10 minutes to Timberline Mountain and Canaan Valley Resort makes it a convenient location for skiing, snowboarding, and all of your favorite winter activities. With year-round adventures to be had, this is the hikers, bikers, sightseers, and art-lovers destination! Play all day and enjoy a relaxing evening with everything you need at Roxy’s Retreat!

Darling Duplex

*NO cleaning fees in 2025!* Hands down BEST Value in Hagerstown and Surrounding areas Perks include: •Pet friendly •Entire private home •Central HVAC (dual units) •Walk-in shower •Fenced-in backyard •Full size washer and dryer (with essentials!) •Dishwasher/Garbage disposal •Piano •Multiple bathrooms and beds • and so much more! Comfy 100 year old duplex minutes away from downtown. Remodeled kitchen and posh upstairs bath. A short walk to the beautiful Hagerstown city park.

Artful Lodger

This comfy little get away is nestled in the woods, yet still in town. Walk or drive into Davis for food and drink. • Siriannis Pizza has the best pizza. • Stumptown Ales award winning craft IPAs, use growler • Blackwater Falls State Park is beautiful. Two minutes away. • The Billy Motel has the coolest bar & food. • Canaan Valley Resort State Park (golf, ski, dine) • Timberline Mountain ski area (brand new ownership) • White Grass Ski Touring Center (cross country skiing)

Cozy Historic Town Home

Cozy town home in the Historic District just steps from vibrant, happening Market Street. Restaurants, shops, entertainment, and craft beverage establishments abound. Just a short walk to blossoming East Street and Shab Row for more dining and shopping options. Convenient to historical parks, mountain recreation areas, wineries, breweries, distilleries, wedding venues, craft fairs, farmer's markets, and local events and attractions. Free parking included!

Downtown Artist's Cottage

Stylish ★ Clean ★ Downtown Artist's Cottage ★ Walk to Everything Located in historic downtown Frederick, this relaxing home is a perfect getaway close to all local attractions. Built-in 1894, this charmer is an ideal get-away for a couple or a family, sleeping up to 6 people. This welcoming cottage has all modern amenities and preserved historic details, charming artsy decor, a covered front porch, back terrace, and a nice size fenced-in yard.

Modern Elegance in Historic Old Town Winchester

Just a block and a half from the Old Town Winchester pedestrian mall, this historic beauty with modern elegance is sure to please. You are within walking distance of quaint shops, great restaurants, The Brightbox Theater, and The Shenendoah Discovery Museum. Spend the day touring the areas great wineries or enjoying Skyline Drive, and then return to enjoy a great night out, or an evening at home making dinner in the spacious modern kitchen.

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.

1865 2BR Retreat on Market• Walk & Dine• Park Free

Step outside to Carroll Creek, breweries and award-winning dining just steps from our 1865 retreat. Free private parking means you can leave the car and explore on foot. Inside you’ll find two King bedrooms, fast Wi-Fi, fully-equipped kitchen, washer/dryer and smart TV—everything for a fuss-free stay. • Historic charm with modern comforts • Walk score 95 • Self-check-in Love the vibe? Book your dates today!

Pet Friendly: Ping Pong Table, Fire Pit & Fence

Experience the best of Frederick from our charming three-bedroom house, perfect for exploring downtown on foot or by bike. Enjoy the comfort of a well-equipped kitchen and relax in our fenced yard, a true dog paradise. Conveniently located just 0.6 miles from the Maryland School for the Deaf and 3 miles from Fort Detrick.