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Compare 230 Vacation Homes in Middletown with updated reviews, rates, and availability.

Trailside Retreat in breathtaking Western Loudoun

10.0 out of 10, Exceptional, (44)
"We had a full family 4 day retreat and Jill’s place was perfect. Lots of room, beds were so comfy and contained all the kitchen and bathroom supplies we needed. Everything was clean - they even had some toys for the kids. Great location…convenient to all activities, restaurants and hiking trails. We would definitely book again. 5 stars!"
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 SAR 375
SAR 1,509 total
includes taxes & fees
12 Mar - 13 Mar
White House Inn - Historic Home in Harpers Ferry!

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

9.8 out of 10, Exceptional, (91)
"The place is so beautiful and so peaceful the views to the river are amazing. We are planing to visit again. We had an excellent time with my friends. Thank you again Scott and Margie. "
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, (112)
"Many thanks to Jill. I can't say how much it matters to have a fantastic host!!! We plan to come back in the near future!"
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 SAR 578
SAR 1,126 total
includes taxes & fees
12 Mar - 13 Mar
Cottage on King | Charming Historic Leesburg Home

*Luxury Condo In Downtown Frederick*

9.2 out of 10, Wonderful, (53)
"The condo was very good for the price and convenience. I think it definitely needs a little TLC with the furnishing and details. The communication for check-in was pretty poor and it took calling VRBO support to get our checkin instructions within 45 minutes of arrival after my messages were ignored for 2 days leading up to arrival. "
The price is SAR 383
SAR 895 total
includes taxes & fees
9 Mar - 10 Mar
*Luxury Condo In Downtown Frederick*

*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, (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

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 SAR 368
SAR 747 total
includes taxes & fees
1 Apr - 2 Apr
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, (78)
"Great location in downtown Frederick. Cozy and comfortable accommodation with great historic vibes and modern amenities. We would definitely stay here again. "
“The Train Depot” 2nd oldest in the US

The Madison

10.0 out of 10, Exceptional, (29)
"Fantastic. We loved it! "
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 SAR 1,500
SAR 2,356 total
includes taxes & fees
7 Mar - 8 Mar
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, (54)
"Multiple generations enjoyed this lovely house with plenty of space, well stocked kitchen, and great location for winery visits. Highlights include extra sleeping space, local coffee provided by the host, and the hottub! Gorgeous views and responsive hosy! "
The price is SAR 375
SAR 1,503 total
includes taxes & fees
9 Mar - 10 Mar
Terra Alta - Incredible River Views and Hot Tub!
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, (91)
"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

Charming "Cream of the Crop" Cape ~❤️of Middletown

10.0 out of 10, Exceptional, (121)
"We had a nice stay in this charming house. Everything we needed to relax, chat, visit, and cook was available and in working order. The beds were comfortable, the shower water hot, and the house was clean and nicely warm -- especially appreciated on these freezing, snowy days! Would stay again and definitely recommend."
The price is SAR 469
SAR 1,046 total
includes taxes & fees
9 Mar - 10 Mar
Charming "Cream of the Crop" Cape ~❤️of Middletown

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 SAR 356
SAR 799 total
includes taxes & fees
9 Mar - 10 Mar
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
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.