Holiday rentals in Hagerstown

*NEW* Elegant Spacious Escape, Serene Wooded Views

Escape to this serene retreat featuring a stunning sunroom bathed in natural light, perfect for morning coffee or evening wine. Huge windows frame peaceful woodland views, bringing the outdoors in. Thoughtfully designed luxe touches—soft linens, high-end finishes, and stylish décor—this home offers comfort and elegance. Whether you’re enjoying the morning views or gathering in the "Fan Cave" for a game or a movie on the large 70" screen TV, it’s the perfect blend of nature, refinement and fun!

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.

Spruce Run Cabin, a wooded retreat on the mountain

The traditional log cabin is located on 25 acres of mostly wooded terrain in the scenic rural countryside of Wolfsville, Maryland, less than an hour and a half from D.C./Baltimore. The hosts live on the property, but the cabin is situated where it feels very private and you do not see the hosts house from the cabin. The cabin faces the woods and there is a private trail down to the creek. Take a break from everyday life, and escape to this unique and quiet retreat in the Catoctin Mountains.

Private Woodland Retreat | Near Downtown Frederick

Escape to a beautiful one-bedroom retreat. The guesthouse has a queen bed, full kitchen, luxurious bathroom with two shower heads, including a rain head, and a queen pull-out sofa bed. Nestled in the woods with a covered porch for morning coffee, yet minutes to downtown Frederick, Civil War sites, Frederick Watershed with cycling trails, Mount St. Mary’s University, Cunningham Falls, Catoctin and Fort Detrick. Free WiFi, and Smart Roku TV’s. Parking for 2 cars is included. Pets are welcome.

Clover Cove

Simple, peaceful, private, & central location. Relax on the back porch, snooze on the hammock, 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.

Private Country Club Home

We are experienced super hosts with over 9 years of hosting. We have a charming mother-in-law suite with your own entrance in an upscale country club development. Features a beautiful large backyard, a fire pit, an outdoor deck and grill, a private living room, a kitchenette, a private bath, and a bedroom. We are just 30 minutes from White Tail Ski Resort and less than an hour to Gettysburg, Antietam Battlefield, the Appalachian Trail, and the C&O Canal. Come join us for a relaxing stay.

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.

The Great Escape Lodge ~ Exquisite Mountain Views

The Great Escape Lodge is a soaring A-frame offering luxury accommodations. Owner designed and custom built in 2022, this luxury getaway is nestled in the stunning Catoctin Mountains with views parallel to those seen on Paramount's hit series Yellowstone. This exquisite residence offers outstanding interior and exterior custom touches and amenities. From the open concept great room to the massive deck with rockers and hot tub, there are endless opportunities to enjoy the scenic views.

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.

Jewel Vinsota Artist's Guesthouse

Less than a mile from the Appalachian Trail, the dog-friendly Jewel Vinsota Artist's Guesthouse is the perfect get-away to explore nature or your artistic leanings. The house is full of original artwork, hand-crafted details, and books on art and architecture. Wander the grounds and find sculpture, ponds, and trails through the woods. Want to hike the entire 40-mile length of Maryland on the Appalachian Trail? Start and end at the Jewel Vinsota and we can drop you off and pick you up.

Turkeyfoot Hideaway!

Turkeyfoot Hideaway is serene retreat and a peaceful escape. This charming cabin has a quiet location with self check in via keypad. We also have walking trails, a lighted fire pit area, gas grill and large deck! We look forward to hosting you! We are just 15 minutes from downtown Chambersburg with lots of unique food and coffee shops! We are just 20 minutes from Hagerstown, MD, just 25 minutes from Whitetail Ski Resort and only 40 minutes from historic Gettysburg! Come find us!

The Crooked Cottage: a Cozy, Curated Escape

You will instantly relax in this stylish, pet-friendly home only 8 mins from I-70, exit 42. Under a canopy of trees find a beautifully landscaped yard with decks and two fire pit areas. Enjoy the well-apportioned kitchen with organic, fair trade coffee. Relax with 2 Roku TVs, games and puzzles, bathe with soaking salts and Turkish towels. For outdoor enthusiasts, pitch your tents. Sit by the wood-stove in the winter, or lay in a hammock when it’s warm. Welcome to The Crooked Cottage!