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
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 217 Vacation Homes in Middletown with updated reviews, rates, and availability.

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

9.8 out of 10, Exceptional, (86)
"We were looking to unplug for a night, and this cottage was the perfect spot! Clean and well kept, calm and quiet surroundings. One note is that the WiFi was not working. We didn’t need it for our trip, but something to keep in mind!"
The price is AED 533
AED 806 total
includes taxes & fees
25 Nov - 26 Nov
Riverside cottage, minutes from historic Harpers Ferry! Private river access!

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

10.0 out of 10, Exceptional, (110)
"This property could not have been more quaint and peaceful. My husband, two dogs and I enjoyed the long weekend, walking the trails and taking in the history of Harper’s Ferry. I would highly recommend this property to anyone looking for a quiet getaway. The location could not be better for seeing the town on foot. The property was clean and so neatly appointed. Breathtaking views! "
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

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

9.8 out of 10, Exceptional, (118)
"Two sisters, a brother and spouses met up in this delightful house in Harpers Ferry. It was spacious and well equipped. There were interesting books and pictures in the house and in all, had a spacious but cozy atmosphere. It waa a nice walk into this quaint, historic town.."
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

Newly constructed 6 bedroom home

10.0 out of 10, Exceptional, (4)
"This new home is beautiful, clean, and well-equipped. The beds were comfortable. Great neighborhood for walks, still under construction right across the street. Host was quick to respond to inquiries. We were surprised to discover that there is a family living in the basement, as we thought we had rented the entire home. Apparently, it is disclosed on the website if you click on "See all rooms and bed details" and look under the 3 bathrooms section that the basement is not part of the...
The price is AED 680
AED 1,604 total
includes taxes & fees
25 Nov - 26 Nov
Newly constructed 6 bedroom home

NEW LISTING! Mountain Chic Retreat by RedAwning

2.0 star property
10.0 out of 10, Exceptional, (1)
"I grew up in Jeff Co, but never explored this area of the county. Great house very peaceful! Only feedback and down side was NO laundry machines on site. "
The price is AED 555
AED 1,657 total
includes taxes & fees
25 Nov - 26 Nov
NEW LISTING! Mountain Chic Retreat by RedAwning

White House Inn - Historic Home in Harpers Ferry!

10.0 out of 10, Exceptional, (25)
"Great location in a very safe neighborhood! House was very roomy with very comfy beds. Would definitely stay here again!! "
White House Inn - Historic Home in Harpers Ferry!

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

9.4 out of 10, Exceptional, (103)
"comfortable, clean and charming townhouse in the heart of downtown Frederick. I especially liked the decor (including a pac man that really works!) and the landscaped outdoor area with seating. "
The price is AED 514
AED 1,152 total
includes taxes & fees
22 Dec - 23 Dec
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

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

9.8 out of 10, Exceptional, (171)
"Wonderful home close to many attractions in western Maryland.It’s any easy drive into Harper’s Ferry, Sherpardstown, and it’s walking distance to the battlefield of Antietam. Check out Little Brick Coffee in the morning and if you enjoy wine visit Antietam Creek Winery. The house itself was like a trip to past with all the modern conveniences.It was very clean and despite being in town it was also very quiet. Thanks, we’ll definitely be back!"
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

Hillside Hideaway in Lowertown Harpers Ferry

9.8 out of 10, Exceptional, (10)
"The house was great, beds were comfy, everything we wanted to see was close by so we could walk, and despite being close to everything it was still quite private. "
Hillside Hideaway in Lowertown Harpers Ferry

Mountain Getaway - 7 beds (2 King) - Large Common Area

10.0 out of 10, Exceptional, (9)
"This place was everything and more. We had quite a large group coming in for a weekend trip, and this place was able to fit all of us. The pictures do not do it justice because this place was beautiful, clean, and spacious. Would love to come back one day!"
Mountain Getaway - 7 beds (2 King) - Large Common Area

Charles Town Townhome: 9 Mi to Harpers Ferry

10.0 out of 10, Exceptional, (8)
"I spent a week in the property and thoroughly enjoyed my stay. The check-in process was very smooth and the home is immediately welcoming. The downstairs is modern and spacious. It is a very family friendly place that is equally suited for single or couple travelers. I love the intentionality of blending a play nook for kids into a gathering area for adults. The upstairs is very comfortable. The master bedroom features a king beg that seemingly hugs you while you sleep. The en suite bath...
Charles Town Townhome: 9 Mi to Harpers Ferry

Private, Relaxing, quite, 3 Bedroom Unit, sleeps 6 to 8 people

10.0 out of 10, Exceptional, (1)
"Nice and clean, easy check in and out. The unit was easy to get to, the neighborhood was quiet and it was easy to get to the highway. We were on our way to Ocean City and needed a stop over in MD. This was a pleasant location, easy to get to and perfect for a one night stop over. It was very clean and neat and the off street parking spot was a nice convenience."
The price is AED 331
AED 705 total
includes taxes & fees
26 Nov - 27 Nov
Private, Relaxing, quite, 3 Bedroom Unit, sleeps 6 to 8 people

Waterfront property in Harpers Ferry - Private River Access

10.0 out of 10, Exceptional, (21)
"Our stay at this vacation home was very enjoyable! The house was clean, well maintained and comfortable. It is located on a nice piece of property with a beautiful view of the Shenandoah River. The owner provided a lot of necessities like bed sheets, bath towels, soap, shampoo and even coffee supplies. The house is up to date and has a nice basement entertainment area. The fire pit area near the river was probably our favorite amenity. We enjoyed it on a couple evenings while enjoying the...
Waterfront property in Harpers Ferry - Private River Access

Terra Alta - Incredible River Views and Hot Tub!

9.8 out of 10, Exceptional, (52)
"Está bien hermosa la casa "
The price is AED 661
AED 1,898 total
includes taxes & fees
1 Dec - 2 Dec
Terra Alta - Incredible River Views and Hot Tub!

Modern Country House on the Shenandoah River

9.8 out of 10, Exceptional, (29)
"Overall was beautiful. Very easy to communicate with the owner. The view was breathtaking. I’d definitely recommend this to my other families and friends. Thanks again for making our stay so pleasant. "
Modern Country House on the Shenandoah River

Hot Tub, Poker Table, River Access & Kayaks and Wineries

9.6 out of 10, Exceptional, (17)
"I stayed with some friends in the house and we had a great time, the beds were comfortable, the house was clean, the outside was quiet and private. We didn’t use the hot tub or the fire pit, but we played cards on the table outside and all in all had a great time."
The price is AED 573
AED 1,522 total
includes taxes & fees
2 Dec - 3 Dec
Hot Tub, Poker Table, River Access & Kayaks and Wineries

Family vacation on a farm near Washington DC, Baltimore, Gettysburg.

10.0 out of 10, Exceptional, (87)
"We were in town visiting family for a few days and had a wonderful stay at the farm. The beauty of the property is breathtaking and you'd be hard pressed to find a more spectacular view from the spacious front porch. Sue and her husband have thought of everything here to make the stay comfortable and complete. Highly recommended!"
Family vacation on a farm near Washington DC, Baltimore, Gettysburg.

ENTIRE 2 BDRM 2.5 BATH Duplex - Mountains, Rivers, Wineries, Breweries, Casino

9.4 out of 10, Exceptional, (135)
"My family enjoyed the spacious, comfortnabel and q house and close proximity to everything harper's Ferry has too offer,"
ENTIRE 2 BDRM 2.5 BATH Duplex - Mountains, Rivers, Wineries, Breweries, Casino

Trailside Retreat in breathtaking Western Loudoun

10.0 out of 10, Exceptional, (36)
"Beautiful home. Nice location Enjoyed our stay very much"
Trailside Retreat in breathtaking Western Loudoun

Relax by the lake, wineries, hiking, history, casino fun just 16-min drive away

10.0 out of 10, Exceptional, (7)
"We had a wonderful time at the house! Took advantage of the hot tub and bon fire pit. It was an amazing way to end the days. The fenced in yard was amazing for our doggies and they loved the property as well. :) The third bed (downstairs) is more of a loft bed, so keep that in mind. My friend is very tiny so it wasn't an issue for her, but my mom wouldn't have been able to get into the space. FANTASTIC SPOT! "
Relax by the lake, wineries, hiking, history, casino fun just 16-min drive away
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

Other property types in Middletown

Countryside Cabin with Mountain Views near Surreybrooke Gardens

10.0 out of 10, Exceptional, (85)
"My husband and I were beyond thrilled with this property. Absolutely incredible and are looking forward to visiting again!"
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, (87)
"Quaint little getaway for the night. Especially beautiful in autumn with the foliage and the season decorations inside the home! "
The price is AED 367
AED 822 total
includes taxes & fees
1 Dec - 2 Dec
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, (25)
"Quaint adorable cabin nestled next to battlefields and short drive to Harpers Ferry. Beautiful deck in back overlooking woods. We hiked at various lookouts and did the ranger talk in town (highly recommend). Magical 3 day 2 nights. Completely relaxed! "
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.