Photo by Doug Kerr

Holiday Rentals in Middletown

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Holiday Rentals in Middletown

Countryside Cabin with Mountain Views near Surreybrooke Gardens

10.0 out of 10, Exceptional, (90)
"Absolutely beautiful cozy and idyllic and Cassandra was extremely responsive! Also very close to amazing hiking at Gambrills park. Ill be back! "
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, (88)
"It is a very quaint property and sed has the rustic cabin feel, the location was not as intimate as we hoped as it is in a regular neighborhood with close primary with neighbors. "
The price is €208
includes taxes & fees
26 Jan - 27 Jan
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

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

10.0 out of 10, Exceptional, (119)
"But the warmth of the home helped our stay."
The price is €272
includes taxes & fees
26 Jan - 27 Jan
Charming "Cream of the Crop" Cape ~❤️of Middletown

Serene Log Cabin Nestled Among the Battlefields

8.2 out of 10, Very good, (26)
"This was a lovely getaway for me and my girlfriend. There were a few issues: the cabin could use a good dusting in kind of obvious spaces, host told us the cleaners hadn’t been in halfway through and that was a tad disconcerting, and I don’t think the listing mentioned how the cabin is so close to the main property. We think the privacy was still pretty good, but it would’ve been nice had that been clearer up front. Overall, a good stay. "
Serene Log Cabin Nestled Among the Battlefields

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (51)
"It was a cozy little tiny house located right on the river. I came in January and it was about 15 degrees outside so I did not get to use the outdoor shower or grill. I was able to enjoy the view of the river from the tiny house and walk outside on the road (not too many cars). If it was any warmer I would have built a fire and sat outside closer to the river. I would love to come back and stay when it was warmer to enjoy the outdoor more. Perfect retreat to reset. Very close to a nearby college...
The price is €109
includes taxes & fees
3 Feb - 4 Feb
❤️ Secluded 1940s Romantic Tiny House on the River

Gorgeous 1840 Log Cabin- Downtown

10.0 out of 10, Exceptional, (124)
"This is my go-to place to stay in Frederick, where I visit a sister often. It is a historic cabin beautifully renovated, very comfortable and clean and in a to die for location: right downtown, close to the night life and restaurants of Market Street but just far enough way so that the property itself is quiet and peaceful. Love it! "
Gorgeous 1840 Log Cabin- Downtown

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

9.8 out of 10, Exceptional, (89)
"This was a perfect clean comfortable place to stay while exploring the Harper's Ferry area. Hosts Scott and Margie are friendly and welcoming"
Riverside cottage, minutes from historic Harpers Ferry! Private river access!

White House Inn - Historic Home in Harpers Ferry!

10.0 out of 10, Exceptional, (27)
"Great location in a very safe neighborhood! House was very roomy with very comfy beds. Would definitely stay here again!! "
The price is €485
includes taxes & fees
30 Jan - 31 Jan
White House Inn - Historic Home in Harpers Ferry!

Walk to Potomac River and downtown Harpers Ferry

10.0 out of 10, Exceptional, (111)
"The house was a perfect size for my group of 10. We stayed for my birthday weekend and the house was very stocked with cleaning supplies, sheets, pillows, towels, etc. Michael was very responsive and even sent a huge list of recommendations in the area. If I'm ever in the area again, I will definitely be staying here!!!"
Walk to Potomac River and downtown Harpers Ferry

Antietam Toll House~ an historic waterfront cabin

9.8 out of 10, Exceptional, (72)
"Had a great time in the cozy cabin for new years. Too cold and rainy to do much outside but it was a perfect spot to get away from everything and turn the cell phones off for two days. Beautiful cabin and loved the fully equipped kitchen."
The price is €271
includes taxes & fees
26 Jan - 27 Jan
Antietam Toll House~ an historic waterfront cabin

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

10.0 out of 10, Exceptional, (111)
"Great communication with host. Cosy house, well equipped kitchen in a great location."
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

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

Rustic Log Cabin with Private Dock on the Lake!

9.6 out of 10, Exceptional, (12)
"Amazing location!!! 18 minutes from a cluster of wineries; quiet and relaxing. Definitely will be visiting again "
The price is €402
includes taxes & fees
27 Jan - 28 Jan
Rustic Log Cabin with Private Dock on the Lake!

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.2 out of 10, Wonderful, (116)
"The hosts are wonderful. I had a great time in their cozy, clean and beautiful place. Highly recommend for a visit to beautiful and historic WV.I particularly appreciated their fondness for dogs. Mine had a great time too!"
RIVERKEEPER INN, Waterfront Property on the Potomac River

Family Friendly Mountain Cabin w/ Steam Shower! Great for Couples.

10.0 out of 10, Exceptional, (54)
"The cabin was very nice and quaint. We had a nice stay. The view from the sunroom is great amazing. The place is very cozy and made for a great night away. "
The price is €276
includes taxes & fees
27 Jan - 28 Jan
Family Friendly Mountain Cabin w/ Steam Shower! Great for Couples.

Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

9.8 out of 10, Exceptional, (53)
"We booked this cabin for a small girls weekend and it was perfect! The view is absolutely amazing! The fireplace is cozy, just make sure you bring lots of wood to keep it going! We also enjoyed using the hot tub each night! The house was clean and in order and communication with Mountain Mama’s was great. "
The price is €425
includes taxes & fees
28 Jan - 29 Jan
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

Snow is HERE! Only five minutes from Liberty Ski Resort.. Come stay with us!

10.0 out of 10, Exceptional, (287)
"We've stayed here multiple times and always have a great time. Very close to Liberty for skiing. Always good communication with the owner and the cabin is cozy and well-stocked. Highly recommend!"
Snow is HERE! Only five minutes from Liberty Ski Resort.. Come stay with us!

Rural Home, Hot Tub, Campfire, Hardwood Floors

9.4 out of 10, Exceptional, (71)
"Lovely house. A couple of rooms were cold but not unbearably cold. The large table in the sun room was awesome for Thanksgiving dinner. We would definitely stay again if we wanted a house in the area."
Rural Home, Hot Tub, Campfire, Hardwood Floors

Secluded Cabin a Stone's Throw From the A.T.!

9.8 out of 10, Exceptional, (18)
"My wife and I stayed for 2 nights. Aside from being off the beaten path, the cabin was clean and welcoming. There was ample room for a larger party with a gaming area downstairs and a larger sitting area/living room upstairs. There were several comfortable sitting areas, a working fireplace, and blankets stashed throughout the house. The kitchen was decent with basic cooking utensils, a dishwasher, microwave, and air fryer. There was a large table for big sit-down meals. We only stayed in one...
The price is €412
includes taxes & fees
6 Feb - 7 Feb
Secluded Cabin a Stone's Throw From the A.T.!

Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin

9.6 out of 10, Exceptional, (50)
"My husband and I along with our 2 small dogs had a wonderful stay at this lovely mountain retreat. The cabin was clean and comfortable and had everything that we needed to cook breakfast and an easy dinner each evening. The property was beautiful with lots of tall old growth trees that were beautiful with the fall colors and even though it was in a community you felt like you were in a secluded mountain retreat because most of the homes were obsured by the trees; and it is on a dead end road...
The price is €289
includes taxes & fees
29 Jan - 30 Jan
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin
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 types of properties in Middletown you may be interested in

Countryside Cabin with Mountain Views near Surreybrooke Gardens

10.0 out of 10, Exceptional, (90)
"Absolutely beautiful cozy and idyllic and Cassandra was extremely responsive! Also very close to amazing hiking at Gambrills park. Ill be back! "
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, (88)
"It is a very quaint property and sed has the rustic cabin feel, the location was not as intimate as we hoped as it is in a regular neighborhood with close primary with neighbors. "
The price is €208
includes taxes & fees
26 Jan - 27 Jan
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Country Inn & Suites by Radisson, Frederick, MD

3.0 star property
8.4 out of 10, Very good, (1007)
"It was a good price for a clean safe place with a good breakfast. The front desk staff were particularly helpful for me with a problem I had that they helped solve. I will stay here again. "
The price is €76
includes taxes & fees
5 Feb - 6 Feb
Country Inn & Suites by Radisson, Frederick, MD
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.

Frequently asked questions

Can I find a holiday rental in Middletown?

Yes, there are holiday rentals close to the most popular sights in Middletown, or you can select a more secluded option if you're looking for a relaxing stay. Middletown is known for its golf courses and riverfront. Make sure you have time to check out the entertainment choices while you're in the area.

What are some of the best holiday rentals that Middletown has to offer?

Riverside cottage, minutes from historic Harpers Ferry! Private river access!: This holiday home rental outside of Middletown offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals will I find in Middletown?

Expedia has 4 holiday rentals for your stay in Middletown.

What can I see and do in Middletown?

South Mountain State Park and Gambrill State Park are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Maryland National Golf Club and Willow Oaks Craft Cider and Wine.

What are holiday rentals like in Middletown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middletown. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have everything you need. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.