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Check prices for these dates

Next weekend
11 Rab. II - 13 Rab. II
In two weeks
18 Rab. II - 20 Rab. II
In one month
2 Jum. I - 4 Jum. I
In two months
30 Jum. I - 1 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, (56)
"The condo is quite spacious, more than expected. We enjoyed the modern touches and private parking is a big plus in downtown Frederick. So close to Carroll Creek and Market St. The hosts are responsive. We highly recommend staying at Gideon Getaways! "
The price is SAR 383
SAR 971 total
includes taxes & fees
7 Apr - 8 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, (43)
"Townhome was in a very convenient location, nicely stocked, roomy, and very comfortable. Communication was fast, friendly and helpful. We came for a girls' weekend and left wanting to come back again soon! No complaints. We'd definitely stay here again and were happy to support a Veteran family!"
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, (93)
"We enjoyed a very comfortable stay. House was very clean and cozy. We were a little surprised by the close proximity to other homes, but other than that it was as described. Hosts were easy to communicate with and created a very welcoming space for us. Thank you! "
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, (113)
"My husband and I thoroughly enjoyed staying in Harper's Ferry. It is a beautiful historic town with many sights to see. This house made it very convenient to have quick access to everything. It was especially useful for time management. We were able to complete our full itinerary that we had planned in advance."
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, (31)
"This was a perfect long weekend stay for two families (4 adults, 4 kids). Comfortable, spacious, and well-equipped house on a beautiful property. Very responsive and helpful host. Would give 6 stars if I could. We hope to be back soon!"
Modern Country House on the Shenandoah River
*In The Heart Of Antietam*
Interior

*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*
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, (104)
"We loved the historic home and its proximity to Carroll Creek and shopping! We were in town for a wedding and were able to walk everywhere we needed to go. "
The price is SAR 525
SAR 1,146 total
includes taxes & fees
20 Apr - 21 Apr
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Cottage on King | Charming Historic Leesburg Home
Terrace/patio

Cottage on King | Charming Historic Leesburg Home

9.4 out of 10, Exceptional, (49)
"Location is great for walking to old town Leesburg. Very busy streets though, keep that in mind. Neighbors and owner were nice and not a problem. Parking can be tight for a larger vehicle. But a Yukon fits. Weather was freezing while we were there (nothing anyone can do about that) so we were stuck inside for our stay). Would be a good stop to base out of to explore historic downtown Leesburg. "
The price is SAR 829
SAR 1,411 total
includes taxes & fees
22 Apr - 23 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, (93)
"What a perfect home for our Thanksgiving celebration! There were so many rooms in which to spread out, the beds were comfortable, and the location was central to necessities. We had a great stay!"
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, (66)
"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, (79)
"Inside was updated. Loved the open space. Good location though it was a drive to downtown shopping and eating. I would stay there again. "
“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, (125)
"The house was excellent. We give it full marks. If we noted problem areas they would have to do with being off season in a tourist town - we had fewer walking-distance dining options than expected. But we did fine driving a few miles. The weekend was a huge success. "
The price is SAR 728
SAR 1,501 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, (122)
"Visited nice restaurants, brew pubs, antique shops. House was perfect for us. Very clean and well equipped. "
The price is SAR 544
SAR 1,142 total
includes taxes & fees
10 Apr - 11 Apr
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)
"I went to the Veterans Hospital in Martinsburg West Virginia for one week on business. I stayed in the renovated schoolhouse for four nights. Clean, nostalgic, historic, spacious and convenient are a few of the adjectives I’d use to describe this quaint little haven. Although I was there alone, I see this as a real learning opportunity for families. I contacted the manager only once and he responded immediately! It was a lovely experience."
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 777
SAR 2,069 total
includes taxes & fees
16 Apr - 17 Apr
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, (93)
"Traveled from Baltimore to get away for a few days. Great location and mountain views. Cozy vintage cabin nicely renovated. "
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, (90)
"Adorable log cabin stay. We enjoyed the quiet neighborhood and cute town with beautiful old homes! It was a nice 3 day respite "
The price is SAR 319
SAR 756 total
includes taxes & fees
7 Apr - 8 Apr
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.