Photo by Doug Kerr

Search Vacation Homes in Middletown

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
18 Apr - 20 Apr
In two weeks
25 Apr - 27 Apr
In one month
9 May - 11 May
In two months
6 Jun - 8 Jun

Compare 284 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 property looks kind of shabby from the rear, but the inside has been modernized and was extra clean. The kitchen was gorgeous. There are a few places where wear and tear were beginning to show and might need some attention. The bedding was adquate, but not luxury, and the light above the sink in guest bath didn't work. Nor did the toaster in the kitchen. So, minor things that just need a little TLC. But as to location, it couldn't have been better for our purposes. We were going to a...
The price is AED 375
AED 962 total
includes taxes & fees
14 Apr - 15 Apr
*Luxury Condo In Downtown Frederick*
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.
Smart TV, fireplace, books

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

10.0 out of 10, Exceptional, (44)
"The rental worked great. Nice location. Very clean and comfortable. "
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
Terrace/patio

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

9.8 out of 10, Exceptional, (95)
"We stayed for 2 nights fishing, and site seeing get away. It was the perfect location!"
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Property grounds

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

10.0 out of 10, Exceptional, (114)
"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
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 AED 514
AED 1,121 total
includes taxes & fees
20 Apr - 21 Apr
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
*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*
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 AED 786
AED 1,369 total
includes taxes & fees
17 Apr - 18 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)
"The property is excellent, and the description of the property is very accurate. Especially the video when you check the property on a computer (the app on a mobile device does not show video). Laura was always prompt to respond to questions or resolve any minor issue we reported. Respond and resolve"
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, (44)
"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, (126)
"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 AED 713
AED 1,449 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 AED 367
AED 931 total
includes taxes & fees
14 Apr - 15 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)
"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 AED 639
AED 1,859 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.
Don't see what you're looking for?
See all available properties in Middletown
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Middletown

Countryside Cabin with Mountain Views near Surreybrooke Gardens
Property grounds

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.
Fridge, microwave, oven, stovetop

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 AED 294
AED 720 total
includes taxes & fees
16 Apr - 17 Apr
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Serene Log Cabin Nestled Among the Battlefields
Exterior

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.