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Compare 226 Vacation Homes in Middletown with updated reviews, rates, and availability.

Trailside Retreat in breathtaking Western Loudoun

10.0 out of 10, Exceptional, (43)
"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)
"Great location in a very safe neighborhood! House was very roomy with very comfy beds. Would definitely stay here again!! "
The price is AED 393
AED 1,514 total
includes taxes & fees
9 Feb - 10 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, (89)
"This was a perfect clean comfortable place to stay while exploring the Harper's Ferry area. Hosts Scott and Margie are friendly and welcoming"
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

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!

Cottage on King | Charming Historic Leesburg Home

9.6 out of 10, Exceptional, (48)
"Is there traffic/road noise? Yes. Can you walk to everything on King St? Also yes. Tradeoffs."
The price is AED 643
AED 1,187 total
includes taxes & fees
10 Feb - 11 Feb
Cottage on King | Charming Historic Leesburg Home

*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*

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, (18)
"Craig was very responsive. The house had everything we needed, plus some nice extras (like the ping pong table and hot tub). If you need a house with a few bedrooms near Harpers Ferry, this is a great option. "
Spacious Quiet Retreat with Hot Tub and Walk to River Minutes to Harpers Ferry

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!

The PINK PEARL in Historic Leesburg

9.6 out of 10, Exceptional, (31)
"Loved the location and ability to sleep 8 people. Great for a weekend stay!"
The PINK PEARL in Historic Leesburg

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 AED 360
AED 732 total
includes taxes & fees
15 Feb - 16 Feb
Private, Relaxing, quite, 3 Bedroom Unit, sleeps 6 to 8 people

“The Train Depot” 2nd oldest in the US

10.0 out of 10, Exceptional, (77)
"The "train depot" is very comfortable, clean, and well designed. It is spacious, allowing us to celebrate our son's birthday with immediate family. The owner has done a great job managing the property and communicates well. We hope to stay there again on our next visit to Frederick."
“The Train Depot” 2nd oldest in the US

The Madison

10.0 out of 10, Exceptional, (28)
"The house was clean and well appointed. Had everything we needed. It had snowed prior to our arrival which made the on street parking a little messy at times. It was also freezing cold so we ended up taking a car most places but it appeared walking to many downtown places would have been nice if weather had permitted. The beds and linens were very nice. The only issue was that they had a problem with the downstairs bathroom that could not be corrected before our arrival. They notified us just...
The Madison

Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg

9.8 out of 10, Exceptional, (46)
"We stayed for two nights while introducing our kids to skiing at nearby Liberty resort. We were fortunate to get 6inches of beautiful snow while we were there, and enjoyed tremendously watching it blanket the trees around us Eileen was very helpful and ensured we had snow shovels and salt! Definitely will be back! "
The price is AED 1,469
AED 2,307 total
includes taxes & fees
9 Feb - 10 Feb
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg

Romantic Stone Cottage Circa 1869-75 acres to Hike

9.2 out of 10, Wonderful, (5)
"Unfortunately we happened to stay when there was a wind storm in the county so we lost power, water and heat for the night. We texted the host to check on candles and/or flashlights but were told to “just use our phones”. (Not really an option when you’ve been traveling all day and phones are almost dead). The cottage is very rustic and not quite as comfortable as the pictures make it out to be. The bed is extremely firm so be aware if you have bad hips or back. There’s also glade plug ins in...
Romantic Stone Cottage Circa 1869-75 acres to Hike

Terra Alta - Incredible River Views and Hot Tub!

9.8 out of 10, Exceptional, (53)
"This was an amazing place to stay. Not too far of a drive from many different activities and a beautiful home. Be warned it is up on a hill so winter stays are more precarious - we ended up leaving a day early out of an abundance of caution due to a large winter storm system moving in. "
The price is AED 367
AED 1,478 total
includes taxes & fees
9 Feb - 10 Feb
Terra Alta - Incredible River Views and Hot Tub!

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

9.6 out of 10, Exceptional, (175)
"We thoroughly enjoyed our stay at the house. It was very clean and fully provisioned. It was really great to stay in such a cool period structure, particularly one that is in such great shape and includes all manner of modern conveniences! The hosts were very welcoming and responsive to questions. Bravo!"
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
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 Middletown

Countryside Cabin with Mountain Views near Surreybrooke Gardens

10.0 out of 10, Exceptional, (90)
"Absolutely beautiful cozy and idyllic and Cassandra was extremely responsive! Also very close to amazing hiking at Gambrills park. Ill be back! "
Countryside Cabin with Mountain Views near Surreybrooke Gardens

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

9.6 out of 10, Exceptional, (88)
"It is a very quaint property and sed has the rustic cabin feel, the location was not as intimate as we hoped as it is in a regular neighborhood with close primary with neighbors. "
The price is AED 294
AED 720 total
includes taxes & fees
11 Feb - 12 Feb
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Serene Log Cabin Nestled Among the Battlefields

8.2 out of 10, Very Good, (26)
"This was a lovely getaway for me and my girlfriend. There were a few issues: the cabin could use a good dusting in kind of obvious spaces, host told us the cleaners hadn’t been in halfway through and that was a tad disconcerting, and I don’t think the listing mentioned how the cabin is so close to the main property. We think the privacy was still pretty good, but it would’ve been nice had that been clearer up front. Overall, a good stay. "
Serene Log Cabin Nestled Among the Battlefields
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.