Townhome holiday rentals in Western Maryland

1880 Cozy Home near downtown

Hidden gem of a house. It was fully renovated down to the studs! This 1880 home is the perfect getaway for a small group or family. Top of the line Nectar mattresses will make it hard to get out of bed. The kitchen is stocked for all your cooking needs. Downtown and Carroll creek are so close you won’t need a car to get to the restaurants and bars! You probably won’t be cooking much, but it’s there if you need it. Cable/internet heating and air conditioning is all brand new. You’ll enjoy it!

Seven springs * Swiss Mt. GOLF&POOL! *free shuttle

Look no further for the perfect RELAXING getaway for any occasion! Our home sleeps 6 adults comfortably with 2 bedrooms, a completely *updated* game room with queen sleeper sofa & 2 full bathrooms! Wake up and enjoy a warm cup of coffee cuddled up next to the fireplace or on our extended deck, and enjoy the spectacular forest views! Our home is perfect for all seasons and includes a community pool, tennis court, & complimentary shuttle that takes you anywhere in the Seven Springs resort!

Charming Historic Frederick Home

Charming 1910 brick home with fenced yard located in the heart of Downtown Frederick, just steps to Frederick's best breweries, beautiful Carroll Creek, and the quaint shops at Everedy Square. The house is the perfect blend of old and new, combining exposed brick/stone, natural light and hardwood floors with modern amenities such as a remodeled kitchen, WiFi, central air, luxury mattresses and cozy furnishings. Family, work, and dog friendly ($50/stay fee; no dogs on furniture; max 2 dogs).

Darling Duplex

*NO cleaning fees in 2025!* Hands down BEST Value in Hagerstown and Surrounding areas Perks include: •Pet friendly •Baby 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 •2 bathrooms and 6 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.

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!

Elegant Home on Carroll Creek + Free Parking!

Garden gate opens onto Carroll Creek! Entirely owner operated, this private and eclectic boutique style home is the ideal spot for visitors who want to stay in the heart of Historic Frederick (Closest Airbnb to Market St. plus Free Parking!) Perfect for a fun filled girls weekend, a romantic getaway, or family trip! Our amenity filled home is set up for your convenience! Just park, drop bags and explore the city! You won’t want to miss this gorgeous historic home away from home!

1880 Victorian TH On Creek near Uptown Happenings!

Historic Victorian townhouse built in 1880. 30 steps to Carroll Creek's Galleria Fountain on the promenade, with festivals, restaurants, antiques, music, theaters, and various types of galleries. Warm historic atmosphere inside with modern central AC and heating, private on-site parking for up to five cars, great wifi, and two Roku TVs. One block to the famous Antique Row, Visitor's Center, Everedy Square, Market St, & Delaplaine Arts Center, & Marc Trains to Washington, DC etc

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!

Positive vibes on Market St

This fully renovated historic home in downtown Frederick, provides for a calm, relaxing place to stay, and is a short walk to Frederick restaurant's, breweries, and local shops. The main level provides a beautiful sitting room, living room, and kitchen. Upstairs you will find 3 bedrooms and an updated bathroom. The back yard is fenced, making it perfect for pets. The house is perfect for a quiet getaway or an outing with friends and family.

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.

1802 Historic Townhome

Historic property built in 1802, 1/2 block from Market Street and downtown Frederick. Parking on street and in nearby parking facility on Court Street. Beautifully restored house with 3 bedrooms and 2 1/2 baths. Backyard with private patio and barbecue grill. Central air and heating and formal dining room and living room. Internet and HD TV with all the amenities. Come enjoy a carefree visit to historic Frederick, close to everything.

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.