Photo by Penni Lowry

Holiday Homes in Hagerstown

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Featured Holiday Homes in Hagerstown

Riverside cottage, minutes from historic Harpers Ferry! Private river access!

9.8 out of 10, Exceptional, (86)
"We were looking to unplug for a night, and this cottage was the perfect spot! Clean and well kept, calm and quiet surroundings. One note is that the WiFi was not working. We didn’t need it for our trip, but something to keep in mind!"
The price is AU$341
includes taxes & fees
25 Nov - 26 Nov
Riverside cottage, minutes from historic Harpers Ferry! Private river access!

Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

10.0 out of 10, Exceptional, (110)
"This property could not have been more quaint and peaceful. My husband, two dogs and I enjoyed the long weekend, walking the trails and taking in the history of Harper’s Ferry. I would highly recommend this property to anyone looking for a quiet getaway. The location could not be better for seeing the town on foot. The property was clean and so neatly appointed. Breathtaking views! "
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

9.8 out of 10, Exceptional, (118)
"The property was just as it was pictured online. We appreciated how clean and orderly it was. Plenty of space and just a short walk into town and to hiking trails."
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

Quiet Highland Home set on gorgeous rolling hills and farm in Western Loudoun

10.0 out of 10, Exceptional, (20)
"What a wonderful stay! This VRBO was perfectly clean and super homey. We loved the decor and welcoming touches. I stayed with my colleagues for a week of offsite meetings, so we appreciated the many bedrooms and bathrooms plus the open meeting space. The wifi was a bit slow at times for our purposes working remotely. I'm sure a more casual user wouldn't have any issues. The location was fantastic. So peaceful and secluded feeling, but in reality just a short drive to Purcellville and Leesburg....
Quiet Highland Home set on gorgeous rolling hills and farm in Western Loudoun

Newly constructed 6 bedroom home

10.0 out of 10, Exceptional, (4)
"This new home is beautiful, clean, and well-equipped. The beds were comfortable. Great neighborhood for walks, still under construction right across the street. Host was quick to respond to inquiries. We were surprised to discover that there is a family living in the basement, as we thought we had rented the entire home. Apparently, it is disclosed on the website if you click on "See all rooms and bed details" and look under the 3 bathrooms section that the basement is not part of the...
The price is AU$680
includes taxes & fees
25 Nov - 26 Nov
Newly constructed 6 bedroom home

NEW LISTING! Mountain Chic Retreat by RedAwning

2.0 star property
10.0 out of 10, Exceptional, (1)
"I grew up in Jeff Co, but never explored this area of the county. Great house very peaceful! Only feedback and down side was NO laundry machines on site. "
The price is AU$702
includes taxes & fees
25 Nov - 26 Nov
NEW LISTING! Mountain Chic Retreat by RedAwning

Breathtaking views with an indoor private pool, come escape with us

9.8 out of 10, Exceptional, (240)
"Great place to relax & enjoy! We loved the pool & hot tub as well abundant indoor/outdoor space. There was a musty smell that lingered on all my clothes and I stayed in the very top floor master & put my clothes in dresser and closet. You may need a dehumidifier in that closet…."
Breathtaking views with an indoor private pool, come escape with us

White House Inn - Historic Home in Harpers Ferry!

10.0 out of 10, Exceptional, (25)
"Perfect property for 5 adult women who love to have their own room! Plus each of us could have our own bathroom! Lots of good gathering space but plenty of places for solitude. Great hiking. Awesome stay"
White House Inn - Historic Home in Harpers Ferry!

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

9.4 out of 10, Exceptional, (103)
"comfortable, clean and charming townhouse in the heart of downtown Frederick. I especially liked the decor (including a pac man that really works!) and the landscaped outdoor area with seating. "
The price is AU$488
includes taxes & fees
22 Dec - 23 Dec
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

9.8 out of 10, Exceptional, (171)
"Wonderful home close to many attractions in western Maryland.It’s any easy drive into Harper’s Ferry, Sherpardstown, and it’s walking distance to the battlefield of Antietam. Check out Little Brick Coffee in the morning and if you enjoy wine visit Antietam Creek Winery. The house itself was like a trip to past with all the modern conveniences.It was very clean and despite being in town it was also very quiet. Thanks, we’ll definitely be back!"
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

Hillside Hideaway in Lowertown Harpers Ferry

9.8 out of 10, Exceptional, (10)
"The house was great, beds were comfy, everything we wanted to see was close by so we could walk, and despite being close to everything it was still quite private. "
Hillside Hideaway in Lowertown Harpers Ferry

4BR, 4BA, Amazing Indoor Pool, EV charger, ~10 acres retreat, next to Park

10.0 out of 10, Exceptional, (25)
"Our family met here for a weekend getaway. The house is amazing and is stocked with everything you need! The pool room is great, the patio out back has firepits for you to sit around at night, and the kids enjoyed riding their bikes on the property and at the park. The views are beautiful and the beds were comfortable.We brought most of our food with us, but there are stores about 15 minutes away. Its a perfect spot to unplug and relax. "
The price is AU$1,335
includes taxes & fees
8 Dec - 9 Dec
4BR, 4BA, Amazing Indoor Pool, EV charger, ~10 acres retreat, next to Park

Mountain Getaway - 7 beds (2 King) - Large Common Area

10.0 out of 10, Exceptional, (9)
"This place was everything and more. We had quite a large group coming in for a weekend trip, and this place was able to fit all of us. The pictures do not do it justice because this place was beautiful, clean, and spacious. Would love to come back one day!"
Mountain Getaway - 7 beds (2 King) - Large Common Area

Charles Town Townhome: 9 Mi to Harpers Ferry

10.0 out of 10, Exceptional, (8)
"Great House"
Charles Town Townhome: 9 Mi to Harpers Ferry

Modern Spacious House With Spectacular Views

10.0 out of 10, Exceptional, (61)
"Visit was amazing...first time to Pennsylvania. What a beautiful piece of property, had fun watching the deer in the morning, opening the windows to fresh air. Very peaceful and a moving experience at the battlefield. We loved it."
Modern Spacious House With Spectacular Views

Oldtown Guesthouse

10.0 out of 10, Exceptional, (15)
"Great place to stay. Location was great for our visits to the Western Maryland Scenic Railroad and the Potomac Eagle Scenic Railroad. Host prepared a welcoming, well appointed home for our stay. Very clean and well maintained."
The price is AU$272
includes taxes & fees
11 Dec - 12 Dec
Oldtown Guesthouse

SKI YA LATER Whitetail

9.8 out of 10, Exceptional, (7)
"My family and I Stayed at Ski Ya Later this weekend. Pros: Great location directly next to Whitetail Ski resort and a short drive to the town of Mercersburg. The beds are very comfortable. The place is modern, decorated very nicely. Check in was a breeze. Nice TV, Chargers galore. Spacious- there were four of us (2 adults , 2 teens) but the place can easily sleep up to 8. Cons: We we’re very disappointed with the lack of cleanliness / cleaning service that occurred prior to our visit. I took...
SKI YA LATER Whitetail

Private, Relaxing, quite, 3 Bedroom Unit, sleeps 6 to 8 people

10.0 out of 10, Exceptional, (1)
"Nice and clean, easy check in and out. The unit was easy to get to, the neighborhood was quiet and it was easy to get to the highway. We were on our way to Ocean City and needed a stop over in MD. This was a pleasant location, easy to get to and perfect for a one night stop over. It was very clean and neat and the off street parking spot was a nice convenience."
The price is AU$298
includes taxes & fees
26 Nov - 27 Nov
Private, Relaxing, quite, 3 Bedroom Unit, sleeps 6 to 8 people

Charming mountaintop cabin with hot tub, pool table, and breathtaking views

9.8 out of 10, Exceptional, (187)
"Enjoyed our stay. Very quiet as the summer season was over. Rained most of the time we were there as remnants of hurricane Helena passed thru. We spent a lot of time just relaxing, hot tubbing between rain drops and hanging out on the covered deck (our favorite spot). Pool table room very nice. Huge bathroom downstairs. Area was nice with town close by, just down the very windy road. No complaints, would recommend to friends."
Charming mountaintop cabin with hot tub, pool table, and breathtaking views

Waterfront property in Harpers Ferry - Private River Access

10.0 out of 10, Exceptional, (21)
"Our stay at this vacation home was very enjoyable! The house was clean, well maintained and comfortable. It is located on a nice piece of property with a beautiful view of the Shenandoah River. The owner provided a lot of necessities like bed sheets, bath towels, soap, shampoo and even coffee supplies. The house is up to date and has a nice basement entertainment area. The fire pit area near the river was probably our favorite amenity. We enjoyed it on a couple evenings while enjoying the...
Waterfront property in Harpers Ferry - Private River Access
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Hagerstown

Dreamtime - Modern A-frame Cabin w/ Hot tub

10.0 out of 10, Exceptional, (34)
"The cabin was in a beautiful community and setting with a fabulous outdoor area facing the woods. Many amenities in the home that made our stay easy with nicely renovated interior. Owner was very willing and able to offer help with anything and was receptive to feedback. Thank you!"
Dreamtime - Modern A-frame Cabin w/ Hot tub

Secluded Pet-Friendly High-Tech Log Cabin in the Woods

9.6 out of 10, Exceptional, (165)
"I enjoyed every peaceful moment I was there! Living near, and working in a big city is loud and stressful. This was just what the Dr. ordered! Beautiful home in a beautiful setting with great amenities. Loved the lower level deck and propane fire pit that was ready to use! My older dog had a few problems traversing the steps but he loved being there as well!!! Already booked another stay! "
Secluded Pet-Friendly High-Tech Log Cabin in the Woods

Countryside Cabin with Mountain Views near Surreybrooke Gardens

10.0 out of 10, Exceptional, (85)
"My husband and I were beyond thrilled with this property. Absolutely incredible and are looking forward to visiting again!"
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.