Photo by Doug Kerr

Middletown Holiday Rentals

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Holiday Rentals in Middletown

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 AU$398
includes taxes & fees
18 Feb - 19 Feb
Charming "Cream of the Crop" Cape ~❤️of 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 AU$320
includes taxes & fees
18 Feb - 19 Feb
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, (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, (53)
"The cabin was perfect for a few days of writing and reflecting! Everything was very clean and it was easy communicating with the owner. The house is not "secluded" as there are neighboring houses on two sides and if I hadn't brought an ax/saw to cut my own dry wood enjoying a fire wouldn't have been possible. But overall a lovely stay and I look forward to going again!"
The price is AU$176
includes taxes & fees
24 Feb - 25 Feb
❤️ Secluded 1940s Romantic Tiny House on the River

Cozy Quiet Cabin Near Historic Gettysburg / Liberty Mountain Resort

10.0 out of 10, Exceptional, (1)
"The secluded and pristine property was an absolute joy to come back to after a long day on the mountain. The constant sound of the babbling creek just steps away from the back deck created the perfect setting for a wonderful mountain getaway. Also, our dog loved roaming the land and seeing the occasional Deer grazing in the woods. I highly recommend booking here. If we ever come back to ski at Liberty resort, this will be the first place I look for to stay in!"
Cozy Quiet Cabin Near Historic Gettysburg / Liberty Mountain Resort

*Modern Condo In Downtown Frederick*

9.4 out of 10, Exceptional, (48)
"Great stay "
The price is AU$382
includes taxes & fees
23 Feb - 24 Feb
*Modern Condo In Downtown Frederick*

Terra Alta - Incredible River Views and Hot Tub!

9.8 out of 10, Exceptional, (53)
"This was an amazing place to stay. Not too far of a drive from many different activities and a beautiful home. Be warned it is up on a hill so winter stays are more precarious - we ended up leaving a day early out of an abundance of caution due to a large winter storm system moving in. "
The price is AU$645
includes taxes & fees
20 Feb - 21 Feb
Terra Alta - Incredible River Views and Hot Tub!

Walk to Historic Harpers Ferry! Beautiful Views.

10.0 out of 10, Exceptional, (39)
"A spacious and very nice home located in a great location - walking distance to the best brewery and the best bakery in the area. Looking forward to visiting again soon! "
Walk to Historic Harpers Ferry! Beautiful Views.

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

Cozy 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 AU$478
includes taxes & fees
24 Feb - 25 Feb
Cozy Mountain Cabin w/ Steam Shower. Great for Couples!

Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!

10.0 out of 10, Exceptional, (9)
"The house is well maintained and furnished, and the outdoor space is lovely. We had a great weekend in Leesburg and would come again. "
The price is AU$556
includes taxes & fees
25 Feb - 26 Feb
Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!

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

9.8 out of 10, Exceptional, (90)
"We had a wonderful stay at the Riverside cabin. With a beautiful view, perfect deck for reading, and a quiet house to get away in. So close to town and activities provided for a wonderful getaway. "
Riverside cottage, minutes from historic Harpers Ferry! Private river access!

Beautiful, Spacious Historic Victorian Near Ski Liberty

9.8 out of 10, Exceptional, (53)
"This was the 2nd year our group of families stayed at this home, and it was more perfect than last year. We arrived Friday last afternoon and evening, and everything was as described. Saturday, a quick 10 minute drive and we were at the slopes for a ski day at Liberty Resort. The proximity is perfect, so in the evening, we drove the teems back for more skiing while the adults hung out at the house. Sunday was a beautiful and perfect snow day. We had planned on a chill games day at the house, and...
Beautiful, Spacious Historic Victorian Near Ski Liberty

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

10.0 out of 10, Exceptional, (32)
"In a town with relatively few accommodations, this house is a standout. A new kitchen and bathroom enhance the charm of the wood floors and original staircase. It's well-located too--just a few walkable blocks from downtown Frederick. The three of us each had our own bedroom and the layout was perfect. Ed was so responsive both before and during our stay. I highly recommend this property if you're looking to spend time in Frederick."
The price is AU$428
includes taxes & fees
18 Feb - 19 Feb
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

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!!

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 AU$285
includes taxes & fees
19 Feb - 20 Feb
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin

Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!

10.0 out of 10, Exceptional, (25)
"What a great home. The host obviously took the extra steps to make sure guests are comfortable and well cared for. Very cozy!"
The price is AU$450
includes taxes & fees
23 Feb - 24 Feb
Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!

Happy Harbor | Mtn + Riverside w/ Game Room + Water Hole!

8.8 out of 10, Excellent, (21)
"Our large family loved coming together at this beautiful home! We enjoyed sitting around the large kitchen and beautiful living room while the teens and kids enjoyed the game room and the basketball area. We also loved having a large property to explore"
Happy Harbor | Mtn + Riverside w/ Game Room + Water Hole!

ROMANTIC GETAWAY : Relax In Our Outdoor Spa This Winter !

10.0 out of 10, Exceptional, (136)
"This was a great place to stay to getaway and have privacy. The Host was so kind and went out of her way when I was not feeling well. It was extremely clean and you can even use the pool and spa. I would highly recommend staying there and it can accommodate more than just 2 people. We would definitely stay there again! Karen Meck"
ROMANTIC GETAWAY : Relax In Our Outdoor Spa This Winter !
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

Country Inn & Suites by Radisson, Frederick, MD

3.0 star property
8.4 out of 10, Very good, (1009)
"Great!"
The price is AU$126
includes taxes & fees
24 Feb - 25 Feb
Country Inn & Suites by Radisson, Frederick, MD

Country Inn & Suites by Radisson, Hagerstown, MD

3.0 star property
8.6 out of 10, Excellent, (1063)
"Excellent"
The price is AU$172
includes taxes & fees
2 Mar - 3 Mar
Country Inn & Suites by Radisson, Hagerstown, 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?

Gambrill State Park and Washington Monument 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 South Mountain State Park.

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.