Townhome holiday rentals in Western Maryland

Victorian Home On Carroll Creek by Uptown Events!

Historic Victorian townhouse built in 1880. Free early check/checkout (usually possible). 40 steps to The Banyan music/events. Beside Carroll Creek promenade, with festivals, restaurants, antiques, music, theaters, and galleries. Warm historic atmosphere inside with modern central AC and heating, private on-site parking for up to five cars, great wifi, and two internet TVs. One block to famous Antique Row, Visitor's Center, Everedy Square, Market St, Arts Center, Marc Trains to Washington, DC.

Hidden Valley Haven - Spacious cozy home

Looking for a mountain getaway? Escape to Hidden Valley! 3 Bedrooms | 2.5 Baths Conveniently located next to Hidden Valley Resort and Golf Course, 15 minutes from Seven Springs. Easy access to gorgeous hiking/biking/snowshoeing trails and ski slopes. A short drive to Fallingwater and Ohiopyle for picturesque views. Whether it’s you and a special someone or a party of 10, this place is a perfect escape! PLEASE NOTE: When traveling in the summer, this home, like many others, does NOT have A/C.

Garden Retreat on Carroll Creek + Free Parking!

Built in 1860, our historic home is the perfect retreat! Garden gate opens onto Carroll Creek, Free on site parking. Entirely owner operated, this private, 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.) Perfect for a fun filled girls weekend, a romantic getaway, or family trip! Just park, drop bags and explore the city! You won’t want to miss this gorgeous amenity filled historic home away from home!

Bring your Pet! Arlington Cozy & Clean Home!

Bright and artsy duplex, located minutes away from Fort Myer, Army Navy Country Club and Golf, Pentagon City Mall, Ballston and Clarendon. 12 minute drive to the White House! Free street parking A fresh sparkling clean & updated unit with new modern style kitchen. Fun procured art work and posters- locally sourced furniture for a private and personal relaxing and peaceful stay close to the heart of Washington DC. You will have a nice private, gated and fenced backyard for your morning coffee.

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 2026!* 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.

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!

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.

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.

Heart of Harpers Ferry: 1800s, Walkable, Dogs OK

BellaRosa at Rose Trellis is a 1840 home with original heart pine floors and real character. The best dining in Harpers Ferry is across the street: Snallygaster's Cafe and Kelly's Farm Kitchen. The Barn has live music throughout the week. We've got plenty of parking, but you won't need your car. The national park, trails, and river are all close by. Harpers Ferry is dog-friendly. Your pup is welcome here, too.