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Check prices for these dates

Next weekend
2 Jum. I - 4 Jum. I
In two weeks
9 Jum. I - 11 Jum. I
In one month
23 Jum. I - 25 Jum. I
In two months
20 Jum. II - 22 Jum. II

Compare 285 Vacation Homes in Middletown with updated reviews, rates, and availability.

*Luxury Condo In Downtown Frederick*
Smart TV

*Luxury Condo In Downtown Frederick*

9.0 out of 10, Wonderful, (58)
"Clean & plenty of room. "
The price is SAR 383
SAR 970 total
includes taxes & fees
28 Apr - 29 Apr
*Luxury Condo In Downtown Frederick*
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.
Property grounds

Walk to Harpers Ferry! Dog-friendly. Beautiful Views.

10.0 out of 10, Exceptional, (45)
"Location and house was just as described. Would highly recommend staying here if your looking for a location close to Harper's Ferry."
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
Miscellaneous

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

9.8 out of 10, Exceptional, (97)
"We had great time fishing, canoeing and sightseeing. We visited Charles Town and went on the night time Ghost Tour. This area is loaded with Civil war history.The fish were hiding but the weather was perfect.Scott was a great host. "
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Exterior detail

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

10.0 out of 10, Exceptional, (116)
"Jill was ver communicative and the home was well equipped. Couldn’t have been more ideal."
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Property grounds

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

9.6 out of 10, Exceptional, (91)
"Great family stay! Highly recommend "
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Modern Country House on the Shenandoah River
Property grounds

Modern Country House on the Shenandoah River

9.8 out of 10, Exceptional, (32)
"The views are beautiful and the house was the perfect size for a group of 7 friends. We had a great time!"
Modern Country House on the Shenandoah River
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

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

9.4 out of 10, Exceptional, (105)
"The house was quaint and so close to everything. My family and I had a great stay. There were a few things that were missing, but we really enjoyed our stay. "
The price is SAR 525
SAR 1,129 total
includes taxes & fees
18 May - 19 May
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
*In The Heart Of Antietam*
Interior

*In The Heart Of Antietam*

9.4 out of 10, Exceptional, (84)
"Cute house with a lot of character. Sat on the front porch and watched everybody go to the ice cream shop. Perfect place to be to get to all of the attractions. The Tavern in town is a great place to eat with a nice atmosphere. House was clean and organized. The only thing I could recommend would be that they have a Keurig in the kitchen"
*In The Heart Of Antietam*
Cottage on King | Charming Historic Leesburg Home
Terrace/patio

Cottage on King | Charming Historic Leesburg Home

9.4 out of 10, Exceptional, (50)
"My husband, mother and I had a great stay at the Cottage on King. It’s tiny but we loved it. It’s beautifully decorated and you can’t get much better in terms of location. There were plenty of towels and other amenities to make for a comfortable stay. The beds and pillows were comfortable- not amazing but slept fairly well. You can hear the traffic but it didn’t bother us. "
The price is SAR 720
SAR 1,311 total
includes taxes & fees
28 Apr - 29 Apr
Cottage on King | Charming Historic Leesburg Home
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Fridge, microwave, oven, stovetop

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

9.8 out of 10, Exceptional, (94)
"We used this beautiful home for a history trip of DC landmarks and regional Civil War Battlefields. The location was great. The drive into DC averaged about an hour and 45 minutes in the mornings due to traffic, but all the other Civil War destinations were much less and the house is large and very well maintained. The family loved sitting in the hot tub each night after a long day of walking and had the extra pleasure of a herd of deer that greeted us each night next along side the driveway...
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Walk to the canal and downtown!!! Cozy 1880 Fully Renovated townhome<br>
Fridge, microwave, oven, stovetop

Walk to the canal and downtown!!! Cozy 1880 Fully Renovated townhome<br>

10.0 out of 10, Exceptional, (67)
"Danny's house provided the perfect base for exploring the Frederick area. The house itself is charming, spotlessly clean, and nicely decorated "
Walk to the canal and downtown!!! Cozy 1880 Fully Renovated townhome<br>
Charles Town Home w/ Private Pool & Hot Tub
Pool

Charles Town Home w/ Private Pool & Hot Tub

10.0 out of 10, Exceptional, (43)
"This is our third year staying in this house and we love it. The company accommodates our requests and is quick to respond if we need anything. The house itself is laid out perfectly for what we need with lots of rooms for both kids and adults. "
Charles Town Home w/ Private Pool & Hot Tub
Waterfront property in Harpers Ferry - Private River Access
Property grounds

Waterfront property in Harpers Ferry - Private River Access

10.0 out of 10, Exceptional, (24)
"Home was great and clean! Matt communicated well and was quick to respond to any questions. Loved being close by to historic Harper’s Ferry! Had a wonderful time at Antietam. Had numerous deer sightings close to the property in the evenings. Would definitely stay here again! A"
Waterfront property in Harpers Ferry - Private River Access
“The Train Depot” 2nd oldest in the US
Exterior

“The Train Depot” 2nd oldest in the US

10.0 out of 10, Exceptional, (80)
"In town for my Sister’s wedding. Stayed here for the weekend. Danny, the host, was easy to communicate with. Place was charming and very comfortable. Beds were comfy as advertised. Downtown Frederick is easily walkable, and hwy 70 was easy to get to to branch out further. Will stay here again if available the next time we are in town."
“The Train Depot” 2nd oldest in the US
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.
Exterior

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

9.8 out of 10, Exceptional, (127)
"Great little house for a family gathering, well stocked, and a short (but steep!) walk into the historic district. Great hiking without moving the car on the C&O."
The price is SAR 728
SAR 1,488 total
includes taxes & fees
1 May - 2 May
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.
*Daley's Doll House At Antietam*
Property grounds

*Daley's Doll House At Antietam*

9.8 out of 10, Exceptional, (93)
"This is a terrific place in an ideal location. It's within walking distance of great eateries, historical sites, and has, in fact, an interesting history itself. The furniture is comfortable, the place is cozy, and we loved the fenced-in backyard. It couldnt have been more perfect for us and our four-legged friends. "
*Daley's Doll House At Antietam*
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Property grounds

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

9.8 out of 10, Exceptional, (176)
"It was such a treat to stay in this unique old house. The basement is built right into the rock hill! The house is comfortable and convenient even though it has seen so many years. The hosts did a great job decorating and taking care of it. We would love to come back on a warmer weekend and enjoy the yard. "
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Charming "Cream of the Crop" Cape ~❤️of Middletown
Terrace/patio

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

10.0 out of 10, Exceptional, (123)
"It was a great house for our family on nice property with a Mountain View in back deck . Quiet and peaceful. We hope to stay again next year too"
The price is SAR 544
SAR 1,121 total
includes taxes & fees
4 May - 5 May
Charming "Cream of the Crop" Cape ~❤️of Middletown
Renovated WV Schoolhouse: History Buff’s Heaven!
Exterior

Renovated WV Schoolhouse: History Buff’s Heaven!

10.0 out of 10, Exceptional, (46)
"The stay was very nice. The school house was clean and well stocked. The community was quiet and close to both nearby national parks which was the reason for our visit. It was a perfect place to retire after a long day of history lessons and great food from the local taverns to a very comfortable bed! We would certainly stay there again."
Renovated WV Schoolhouse: History Buff’s Heaven!
White House Inn - Historic Home in Harpers Ferry!
Terrace/patio

White House Inn - Historic Home in Harpers Ferry!

10.0 out of 10, Exceptional, (29)
"Lovely place full of charm but updated enough to be very comfortable and big enough for many people to spread out.Harpers Ferry is a great little town less than an hour from IAD and close to hiking, biking, history, and good food and drink!THX"
The price is SAR 979
SAR 2,352 total
includes taxes & fees
4 May - 5 May
White House Inn - Historic Home in Harpers Ferry!
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
Exterior

Countryside Cabin with Mountain Views near Surreybrooke Gardens

10.0 out of 10, Exceptional, (95)
"The cabin, the property, the gardens were magical. It was quiet and very peaceful.Surreybrook gardens are a site to behold and their shop has so many wonderful things at reasonable prices.Home made scones were in the freezer when we got there and supplied specialty teas were enjoyed with them. We are so grateful we found this cabin. "
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Interior

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

9.6 out of 10, Exceptional, (93)
"The cabin was very nice and clean. We enjoyed the stay and were able to see and do everything we planned to. "
The price is SAR 281
SAR 716 total
includes taxes & fees
30 Apr - 1 May
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Serene Log Cabin Nestled Among the Battlefields
Exterior detail

Serene Log Cabin Nestled Among the Battlefields

8.2 out of 10, Very Good, (27)
"Our overall experience was nice and relaxing place to be. However, during the cold months. The second floor was warm enough to sleep, but the first floor was very cold, especially when it gets down to 19 at night when there’s no heat because all the heat travels to the second floor/loft. There was a space heater, but didn’t realize it until after we left. The host was easy to get a hold of through messages. The only recommendation I would say is maybe put a firebox insert in the fireplace to...
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.