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Search Vacation Homes in Middletown

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Compare 212 Vacation Homes in Middletown with updated reviews, rates, and availability.

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

9.6 out of 10, Exceptional, (89)
"Great year round location. Owners are nearby if issues occur. HIGHLY RECOMMENDED. "
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!

Cottage on King | Charming Historic Leesburg Home

9.6 out of 10, Exceptional, (45)
"Perfect. No complaints at all. Thank you again. "
The price is AED 485
AED 984 total
includes taxes & fees
9 Jan - 10 Jan
Cottage on King | Charming Historic Leesburg Home

Terra Alta - Incredible River Views and Hot Tub!

9.8 out of 10, Exceptional, (52)
"Está bien hermosa la casa "
Terra Alta - Incredible River Views and Hot Tub!

Walk to Potomac River and downtown Harpers Ferry

10.0 out of 10, Exceptional, (110)
"The house was amazing, great views and a great layout that allowed for us to hang as a group or have some privacy. Very convenient to everything we wanted to do; Harper’s Ferry, Ziplining (or rafting based on time of year), and the Brewery that we went to on the last night felt like it was almost walking distance. Definitely recommend and would stay again in a heartbeat. "
Walk to Potomac River and downtown Harpers Ferry

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

10.0 out of 10, Exceptional, (117)
"We were looking for a quiet getaway location from the Black Friday and Small Business Saturday crowds, but also a location that was close to several small towns near the area...and this property checked all boxes! Everywhere you go within 20-30 minutes is a delight for the history, art, music collector, foodie, entertainment, wine, distillery, brewery, or shopping fanatic...a delightful home and one we hope to visit again!"
The price is AED 349
AED 907 total
includes taxes & fees
5 Jan - 6 Jan
Charming "Cream of the Crop" Cape ~❤️of Middletown

Charles Town Home w/ Private Pool & Hot Tub

10.0 out of 10, Exceptional, (40)
"Lots of space for everyone, excellent pool and hot tub"
Charles Town Home w/ Private Pool & Hot Tub

Charming 3-Bedroom Home in historic Harpers Ferry: No Pet or Cleaning Fees!

10.0 out of 10, Exceptional, (13)
"Harper’s Ferry is amazing and the property is in the heart of it. Walk to the historical sites or Trail store. Park and ride is less than 5 mins to catch train to DC. Home has a modernized restoration with beautiful aesthetics inside. Large deck with smokeless firepit. Back yard is gated for pups. Many thoughtful amenities. Professionally clean. Nice owners. 10/10"
Charming 3-Bedroom Home in historic Harpers Ferry: No Pet or Cleaning Fees!

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

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

9.6 out of 10, Exceptional, (174)
"I had a great time at this beautiful historic house. The hosts are so great and helpful! This house is a historic home with so much interesting architecture. The home is in a beautiful location as well! Loved it!"
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

Pet-Friendly Retreat: Relax w/HotTub, Custom FirePit & Walk to Town/Trails!

10.0 out of 10, Exceptional, (11)
"We hosted Thanksgiving weekend at the house and it perfectly accommodated our large group as well as the varying ages (31-89). House is well organized and amenities were all as described. Plenty of dishwater and glasses for a large group although if you are hosting a large meal bring some disposable platters and a cocktail shaker. Few minutes drive to Purcellville which had plenty of options for live sports and other dinners. Beautifully decorated with plenty of space. Also nice to be at the...
Pet-Friendly Retreat: Relax w/HotTub, Custom FirePit & Walk to Town/Trails!

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

9.8 out of 10, Exceptional, (119)
"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.

Spacious Quiet Retreat with Hot Tub and Walk to River Minutes to Harpers Ferry

9.6 out of 10, Exceptional, (15)
"Very accommodating property close to Harper's Ferry with an abundance of beautiful scenery and close to many historical sites."
Spacious Quiet Retreat with Hot Tub and Walk to River Minutes to Harpers Ferry

Gorgeous 1840 Log Cabin- Downtown

10.0 out of 10, Exceptional, (123)
"I come to Frederick a lot and so have stayed at many of the VRBO properties. This property is the best property I have seen in Frederick in terms of comfort and aesthetic appeal. Everything was super nice and classy from the linens to the dishware. It is in an excellent location within a short walk to Market street and the canal. The host is really nice and very accommodating. I strongly recommend it especially if you want to be downtown."
Gorgeous 1840 Log Cabin- Downtown

Harpers Ferry Home w/ Private Pool & Hot Tub!

10.0 out of 10, Exceptional, (3)
"Great girls weekend spot. The view out back was beautiful, and the house was not far from the grocery store or restaurants. We enjoyed being at the house and did not feel the need to stay busy during our stay it was the relaxing weekend we needed. "
Harpers Ferry Home w/ Private Pool & Hot Tub!

Trailside Retreat in breathtaking Western Loudoun

10.0 out of 10, Exceptional, (40)
"This property was beautiful. The house has been updated top to bottom with beautiful finishes. Plenty of room to gather and spread out. Highly recommend."
Trailside Retreat in breathtaking Western Loudoun

Stunning House! Minutes From Shenandoah River

10.0 out of 10, Exceptional, (19)
"Lovely and well maintained home in a quiet neighborhood!"
Stunning House! Minutes From Shenandoah River

Peaceful Home w/ Patio < 2 Mi to Nat'l Park!

10.0 out of 10, Exceptional, (17)
"Everything was perfect, and comfortable. Owners really care about their visitors. Home was walk in perfect for a family long weekend. Happened to be Thurmont's annual colorfest festival, and home pefectly located, nestled away yet close enough for easy walking. Highly recommend. "
Peaceful Home w/ Patio < 2 Mi to Nat'l Park!

ENTIRE DUPLEX!! Views of Shenandoah Mountains and River Wineries and Breweries!

10.0 out of 10, Exceptional, (72)
"Great location, beautiful view, cozy house"
ENTIRE DUPLEX!! Views of Shenandoah Mountains and River Wineries and Breweries!

Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg

9.8 out of 10, Exceptional, (44)
"Stunning property and well-maintained. I only wish we had more time here! Eileen was incredibly accommodating and flexible with our check-in. "
The price is AED 1,469
AED 2,307 total
includes taxes & fees
5 Jan - 6 Jan
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg
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, (88)
"Cozy cabin, wonderful hosts, great location near the AT. Probably the most thoughtful host we’ve had, they’ve thought of everything from breakfast treats and extra linens, even dog treats."
Countryside Cabin with Mountain Views near Surreybrooke Gardens

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

10.0 out of 10, Exceptional, (117)
"We were looking for a quiet getaway location from the Black Friday and Small Business Saturday crowds, but also a location that was close to several small towns near the area...and this property checked all boxes! Everywhere you go within 20-30 minutes is a delight for the history, art, music collector, foodie, entertainment, wine, distillery, brewery, or shopping fanatic...a delightful home and one we hope to visit again!"
The price is AED 349
AED 907 total
includes taxes & fees
5 Jan - 6 Jan
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)
"Quaint little getaway for the night. Especially beautiful in autumn with the foliage and the season decorations inside the home! "
The price is AED 294
AED 724 total
includes taxes & fees
8 Jan - 9 Jan
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.