Holiday rentals in Hagerstown

Furnished luxury studio suite @ “The Franklin”!

Fully furnished luxurious suite equipped to make your stay memorable. Enjoy a stocked kitchen, washer, dryer, covered courtyard, grill, king bed, office area and reserved parking on site. Includes TV, Wi-Fi, central air and heat with remote control, SS appliances, desk, recliners to make your stay comfortable and effortless. Condo boasts a stylish experience at this centrally-located place. Walking distance to Maryland Theater, USPS, several restaurants, coffee houses, and Meritus Ball Park.

Private, relaxing, scenic 2 bdrm unit, Sleeps 1-5

My mother said over and over again, “The most beautiful place in Washington County “. Start your day with a brisk walk on a nearly 1 mile path that surrounds the perimeter of this beautiful farmland property. Enjoy your morning coffee as you listen to the birds. Relax in a rocking chair on the gazebo as you watch the sun go down behind the mountains. Less than 10 min from I 70 and I 81 and 20 min from Whitetail Ski. Don't expect everything brand new, but expect everything to be neat and clean.

Hawks Nest Hagerstown

Hawks Nest is a charming single level home CENTRALLY located in Hagerstown only a stones throw from Hagerstown Community College. Features include a FULL Kitchen (Refrigerator, Microwave, Stove), Primary SUITE with KING-sized bed, walk-in tile shower, and large closet. For your ENTERTAINMENT kick back on a recliner sofa and watch a favorite movie on a Smart HDTV. Surrounded by nature spot some wildlife while you sip your morning cup of coffee or tea in a rocking chair on the front porch.

Unique historic home - Springhouse 1803

If you are looking for a unique place to stay, come visit us at Springhouse 1803. Yes, there really is a spring under the house. After sitting empty for 20+ years, the house has been restored to be lived in again and it has maintained much of its colonial charm. The house has all the amenities you need for a comfortable stay. NOT A PARTY HOUSE, OWNER IS ON SITE in separate house. If you're looking for a day that is blocked, you can inquiry if it's available, see below for more details.

Creekside Retreat at the Jewel Vinsota

Relax in a quiet, curated, pet-friendly art exhibit. Live with paintings & sculptures that are for sale. This garden apartment is tucked into a hillside above a creek, along the Jewel Vinsota Sculpture Trail. Your host/gallery curators live upstairs. The “Artist’s Guesthouse” is next door. The private entrance is down a stone-stepped path. Perfect for 2 w/ the queen bed but room for 3 w/ the living room futon. Fully equipped kitchen. Private charcoal grill and fire pit next to the creek.

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.

Spruce Run Cottage, Farm stay on Catoctin Mountain

The cottage is located on 25 acres of mostly wooded terrain off Highway 17 near Wolfsville, Maryland, less than an hour and a half from D.C. The cottage faces the woods and the private drive down to the creek. There is almost zero light pollution at night so stargazing is incredible from the balcony. The hosts live on the property up the hill in an 1890’s chink log cabin. Although you can see our house, the cottage feels very private and is a quiet comfortable retreat in the hills.

Hamilton Hideaway (Hagerstown, MD)

✨ Welcome to Hamilton Hideaway ✨ Your cozy retreat in Hagerstown's charming North End! Located just 1/2 mile from vibrant downtown and 5 miles from Hagerstown Valley Mall, this private 1-bedroom apartment offers the perfect blend of comfort and convenience. Relax in a stylish, inviting space that comfortably sleeps 4 with a plush Queen bed and a full pull-out sleeper sofa. Hamilton Hideaway is your ideal home base for exploring Hagerstown. Book now and make your stay unforgettable!

Clover Cove

Simple, peaceful, private, & central location. Rural feel relaxing on the back porch; or venture out just minutes to I81 & I70, C&O Canal, Antietam Battlefield NP, Appalachian Trail, Hiking, Wineries, Biking, Festivals, Potomac Rivr, & Meritus Hospital. We reside in a separate area of home. We offer privacy & safety for our guests. Private entrance, bedroom, bathroom, den, kitchenette, driveway parking. Expect to cross paths with our family & dog on the shared back porch/yard.

Oak Hill Private Suite Historic North End

A recently renovated private suite only 1.5 miles from town center. Welcoming ‘walking’ neighborhood of architecturally diverse homes inspired by the Garden City Movement of early 20th C. Near both Interstate 81 and 70, Museum of Fine Arts, Whitetail Ski Resort, New Baseball Stadium, Antietam, Gettysburg, Frederick, C&O bike trail, wineries, outlets. Guests enjoy stays for tourism, conferences, trainings, the MD Int’l Film Festival, JFK 50, family visits and artist retreats.

Minutes from the Mountains, Miles from Reality

Escape the hustle of life and unwind in this clutter-free home that is perfect for relaxing, after work or retreating with friends. Located in a quiet, beautifull neighborhood, this gem offers one-floor accommodations for easy accessibility. Not far from popular attractions such as, Whitetail Resort for skiing and snowtubing, and Greenbriar Beach & Swim, there is something for everyone to enjoy. Don't miss out on discovering all that this charming area has to offer.

Private Country Club Home

I am an experienced super host with eight years of hosting. I have a charming mother-in-law suite with your own entrance in an upscale country club development. Features a beautiful two acre backyard, a fire pit, outdoor deck and grill, private living room, kitchen, bath, and bedroom. We are just 20 minutes from White Tail Ski Resort and less than an hour to Gettysburg, Antietam Battlefield, the Appalachian trail, and C&O Canal. Come join us for a relaxing stay.