Townhome holiday rentals in Western Maryland

Seven Springs Sunridge year-round mountain chalet!

Sleeps 13 Ski in/Ski out walking distance to the slopes! Renovated 3 bed 3.5 bath townhouse with loft! Chalet boasts 2 king, 1 queen, 4 twin and a queen sleeper couch. Twin beds may be pushed together to make 2 full beds. Includes access to a private hot tub, outdoor kitchen, outdoor dining area and two patios! Best slopes in Western PA. There is a 24 hour shuttle provided to the main lodge. There are tons of biking/hiking trails, golf and a pool in the summer. Have fun in the sun and snow!

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).

Stylish 2-Level Duplex with Private Yard/Parking!

Stylish and spacious! Relax and enjoy this well equiped 3BR duplex with private yard and two private parking spots. Downtown Frederick restaurants, pubs, shops, museums and entertainment are just a few blocks away. Main floor living room, dining room, kitchen and half bath. Second floor features 3 BRs and full bath with tub & shower. Perfect for business travelers, or weekend getaways with friends or family. Amenities include keyless entry, fiber optic internet, Samsung TV and washer/dryer.

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.

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

Step outside to Carroll Creek, breweries, shops 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 with free streaming services —everything for a fuss-free, relaxing stay. • Historic charm with modern comforts • Outdoor space with firepit • Walk score 95 • Self-check-in Love the vibe? Book your dates today!

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!

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)

Boutique Stay on Carroll Creek + Free parking!

Stay directly on Carroll Creek in the best Airbnb in Frederick! 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 (garden opens to Carroll Creek!) Perfect for a fun filled weekend, a romantic getaway, 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!

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.