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Holiday Homes in Hagerstown

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Featured Holiday Homes in Hagerstown

Trailside Retreat in breathtaking Western Loudoun

10.0 out of 10, Exceptional, (44)
"We had an excellent stay at Jill’s VRBO! The home was spacious and clean, perfect for a relaxing weekend away. The location also is ideal for going to wineries near Leesburg and Middleburg. And Jill was a very attentive host— she made sure that someone was there to remove the snow from the driveway and responded to any messages we sent promptly."
Trailside Retreat in breathtaking Western Loudoun

Gorgeous 1840 Log Cabin- Downtown

10.0 out of 10, Exceptional, (125)
"This cabin was easy to find, with off-street parking, and near the beautiful downtown area. I travelled with individuals with disabilities and found the spacious layout very accommodating to our needs. The bathrooms, common room, kitchen, and bedrooms gave it the cabin vibe, were comfortable, and had everything we could possibly need. The host was available for any feedback and I would highly recommend this location for families or friends looking to stay in Frederick. "
Gorgeous 1840 Log Cabin- Downtown

White House Inn - Historic Home in Harpers Ferry!

10.0 out of 10, Exceptional, (28)
"We very much enjoyed our stay at this property. Walking distance to Harper's ferry attractions and plenty of room for 5 adults to spread out. We anticipate renting this property in the future for more ladies weekends!"
The price is AU$645
includes taxes & fees
20 Feb - 21 Feb
White House Inn - Historic Home in Harpers Ferry!

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

9.8 out of 10, Exceptional, (90)
"We had a wonderful stay at the Riverside cabin. With a beautiful view, perfect deck for reading, and a quiet house to get away in. So close to town and activities provided for a wonderful getaway. "
Riverside cottage, minutes from historic Harpers Ferry! Private river access!

Walk to Potomac River and downtown Harpers Ferry

10.0 out of 10, Exceptional, (111)
"The house was a perfect size for my group of 10. We stayed for my birthday weekend and the house was very stocked with cleaning supplies, sheets, pillows, towels, etc. Michael was very responsive and even sent a huge list of recommendations in the area. If I'm ever in the area again, I will definitely be staying here!!!"
Walk to Potomac River and downtown Harpers Ferry

Homey 'Ridgetop Retreat' - Walk to Hiking & Biking

10.0 out of 10, Exceptional, (14)
"Cozy spot right by the slopes for easy access. Ski on, or a very short drive to main parking area. Bunk beds were great for the family. HVAC a bit noisy overnight, but overcame it with some white noise."
Homey 'Ridgetop Retreat' - Walk to Hiking & Biking

Charles Town Home w/ Private Pool & Hot Tub

10.0 out of 10, Exceptional, (41)
"Our families decided to rent the property for a getaway close to the DMV. It was easy to check in, get around Charles Town and enjoy the property. Even with an unexpected 6" of snow, we still found time to appreciate everything the property had to offer."
Charles Town Home w/ Private Pool & Hot Tub

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

10.0 out of 10, Exceptional, (111)
"Great communication with host. Cosy house, well equipped kitchen in a great location."
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

Breathtaking! 5 Acre Private Riverfront Cabin in the Mountains!

9.8 out of 10, Exceptional, (48)
"We got a chance to celebrate our family 40 years of marriage with our family and it was an absolute blast. The host was very detailed in his instructions about the property ensuring we had everything we needed throughout our stay.and available to ensure He did so in a timely manner throughout our stay. The kind women cleaning and preparing the home put in extra time and was so sweat and pleasant as we began our stay. In terms of the property, it was well was well equipped and clean and the beds...
Breathtaking! 5 Acre Private Riverfront Cabin in the Mountains!

*Luxury Condo In Downtown Frederick*

9.2 out of 10, Wonderful, (51)
"Very close walk to shopping and restaurants. Comfortable and renovated nicely."
The price is AU$381
includes taxes & fees
18 Feb - 19 Feb
*Luxury Condo In Downtown Frederick*

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

10.0 out of 10, Exceptional, (22)
"Our group of seven was very, very comfortable there. It was nice to have two separate living areas one on the upper floor and one on the lower floor where one area could be the quieter area and the other area could be the louder area. Bedrooms were separate from the main living spaces on both the first floor and the basement which was very nice. Price per value was excellent, and whenever I return to the area, I will happily stay there again if it’s available!"
Quiet Highland Home set on gorgeous rolling hills and farm in Western Loudoun

*In The Heart Of Antietam*

9.6 out of 10, Exceptional, (82)
"House is clean, pleasant with comfortable beds, a serviceable kitchen and nice common space. My husband and 2 adult children were visiting family who live in sharpsburg and their house was pretty full with other visitors. This was a perfect place for us. Highly recommend. "
*In The Heart Of Antietam*

The General's Hideaway near Gettysburg Battlefields, Wineries, Skiing, & Hiking

9.8 out of 10, Exceptional, (47)
"This was just as described! The location was perfect for Gettysburg and Maryland. We were able to go exploring and make a short trip back to relax."
The price is AU$532
includes taxes & fees
23 Feb - 24 Feb
The General's Hideaway near Gettysburg Battlefields, Wineries, Skiing, & Hiking

Gettysburg Getaway! Battlefields/Wineries/Ski!

10.0 out of 10, Exceptional, (32)
"Rented this house for a family ski trip for family - 2 adults and three teenagers for three nights. House was as advertised and had everything we needed - and nice little touches. 15 minute drive from Liberty Ski Resort. Property owner communicated in a timely and thorough manner and was accommodating to questions. Would rent again "
Gettysburg Getaway! Battlefields/Wineries/Ski!

Gruner Bungalow at Otium Cellars

9.8 out of 10, Exceptional, (93)
"It's was great. We visited family in the area. And had our family Christmas together at this place. We played ping pong and pool when we where there. Great location for dogs. Plenty of space to run and play. The house was great as well. Plenty of space for everyone."
Gruner Bungalow at Otium Cellars

Rural Home, Hot Tub, Campfire, Hardwood Floors

9.4 out of 10, Exceptional, (71)
"Lovely house. A couple of rooms were cold but not unbearably cold. The large table in the sun room was awesome for Thanksgiving dinner. We would definitely stay again if we wanted a house in the area."
Rural Home, Hot Tub, Campfire, Hardwood Floors

Spacious Quiet Retreat with Hot Tub and Walk to River Minutes to Harpers Ferry

9.8 out of 10, Exceptional, (19)
"Family and friends surprised my sister for her 40th birthday with a weekend getaway. Host was very responsive and gave great recommendations. House is in a great location, everything was within 15-20 minutes away. Easy check-in process and very clean. Thanks again. "
Spacious Quiet Retreat with Hot Tub and Walk to River Minutes to Harpers Ferry

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

10.0 out of 10, Exceptional, (29)
"The house is gorgeous. You walk through the front doors and immediately see the beautiful heated indoor pool. Our family had a blast in the pool and watching movies in the theater room. The host immediately responded to any questions that we had."
4BR, 4BA, Amazing Indoor Pool, EV charger, ~10 acres retreat, next to Park

Charming 3-Bedroom Home in historic Harpers Ferry: Pet Friendly!

10.0 out of 10, Exceptional, (15)
"We loved our stay here and the property is simply delightful. It's central to all activities in Harper's Ferry, comfortable, well stocked and the host is super responsive! We especially loved the adjacent off-street parking, and although the weather didn't permit, the fenced, private outdoor space is very inviting. Our host was exceptionally responsive to the couple of questions we had and wonderful to work with. We'd definitely rent again! "
Charming 3-Bedroom Home in historic Harpers Ferry: Pet Friendly!

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

7.0 out of 10, Good, (7)
"This property met our needs beautifully. We will stay here again if we come back to the area, for sure"
The price is AU$317
includes taxes & fees
1 Mar - 2 Mar
Private, Relaxing, quite, 3 Bedroom Unit, sleeps 6 to 8 people
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

Cottage w Hot Tub, Pond & Kayaks, Fire Pit, & WiFi

8.8 out of 10, Excellent, (30)
"Tony was an amazing host. The property was home-y and very spacious. Perfect place to accommodate 2 couples and 2 children (or adults who are children at heart). It was a nice little getaway in the woods with easy access to the town. If you’re looking for a place for some great R&R, this is your spot!"
The price is AU$415
includes taxes & fees
18 Feb - 19 Feb
Cottage w Hot Tub, Pond & Kayaks, Fire Pit, & WiFi

Cozy streamside cabin, convenient to Ski Liberty and Gettysburg

9.4 out of 10, Exceptional, (209)
"Good stay over all - everything you could ever need and great views from the bedroom!"
Cozy streamside cabin, convenient to Ski Liberty and Gettysburg

Private, light filled retreat space... with your own pickleball court!

10.0 out of 10, Exceptional, (23)
"We had a wonderful stay at this beautiful property and I can't say enough good things about it! I can't wait to come back! The owners were above and beyond fantastic! The attention to detail and cleanliness were perhaps the best I've experienced Many tha"
Private, light filled retreat space... with your own pickleball court!
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.