Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Mar 20 - Mar 22
In two months
May 1 - May 3
In three months
May 29 - May 31
In four months
Jun 26 - Jun 28

Our top choices for Middletown vacation rentals

Exterior

Vacation Home in Middletown

Charming "Cream of the Crop" Cape ~❤️of Middletown
10.0 out of 10, Exceptional, (142 reviews)
"Love the place will book again"
United States
WAYNE M.
The price is ￥23,544
￥48,083 total
includes taxes & fees
Mar 22 - Mar 23
Charming "Cream of the Crop" Cape ~❤️of Middletown
Interior

Cabin in Middletown

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
9.6 out of 10, Exceptional, (111 reviews)
"I’ve stayed here and will absolutely stay again."
United States
Katherine M.
The price is ￥14,126
￥32,443 total
includes taxes & fees
Mar 11 - Mar 12
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Interior

Cottage in Keymar

Rural & Historic Detour Escape w/ Horses On-site!
3.0 star property
The price is ￥21,190
￥67,746 total
includes taxes & fees
Mar 7 - Mar 8
Rural & Historic Detour Escape w/ Horses On-site!
Fridge, microwave, oven, stovetop

Cottage in Frederick

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
10.0 out of 10, Exceptional, (64 reviews)
"We had a great time. House was very comfortable and location was perfect."
United States
Liz R.
The price is ￥18,223
￥40,613 total
includes taxes & fees
Mar 9 - Mar 10
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Interior

Vacation Home in Fairfield

Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg
9.8 out of 10, Exceptional, (50 reviews)
"Everything was perfect. The property is very cute and comfortable and the host was wonderful!"
United States
Carey K.
The price is ￥56,506
￥90,777 total
includes taxes & fees
Mar 8 - Mar 9
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg
Dining

Vacation Home in Shepherdstown

Exclusive Wooded Chalet w Magnificent River Views
10.0 out of 10, Exceptional, (16 reviews)
"This property was super nice and the property managers were super awesome and accommodating! "
United States
Construction V.
The price is ￥40,019
￥74,324 total
includes taxes & fees
Mar 9 - Mar 10
Exclusive Wooded Chalet w Magnificent River Views
Interior

Cabin in Keedysville

Antietam Creek - Quiet 2 Bedroom Cabin
9.2 out of 10, Wonderful, (89 reviews)
"This was an amazing cabin with a full kitchen so you could cook and enjoy the quiet."
United States
Lina A.
The price is ￥31,392
￥49,747 total
includes taxes & fees
Mar 8 - Mar 9
Antietam Creek - Quiet 2 Bedroom Cabin
Exterior detail

Condo in Hagerstown

Historic & Cozy ~ Near Antietam Battle & WhiteTail
10.0 out of 10, Exceptional, (33 reviews)
"We keep coming back to this rental. It’s a great location, the apartment is cozy and it’s always easy to book and use."
United States
Don H.
Historic & Cozy ~ Near Antietam Battle & WhiteTail
Property grounds

Cabin in Thurmont

Birch Cabin at Hunting Creek Hideaway
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful location. Just what we were looking for."
United States
tony l.
The price is ￥15,257
￥23,659 total
includes taxes & fees
Mar 9 - Mar 10
Birch Cabin at Hunting Creek Hideaway
Terrace/patio

Cabin in Harpers Ferry

Hillside Hideaway in Lowertown Harpers Ferry
10.0 out of 10, Exceptional, (19 reviews)
"The house is in a perfect spot to explore downtown Harpers Ferry! So much history within walking distance and so many beautiful homes. "
United States
Anonymous traveler
Hillside Hideaway in Lowertown Harpers Ferry
Outdoor pool

Apartment in Barnesville

Beautiful, Secluded & Private on 50-acre Estate
10.0 out of 10, Exceptional, (9 reviews)
"Juanita & Zeus were such a pleasure and very accommodating. The suite was clean, the property beautiful and watching the sunset over the mountain in the hot tub was amazing. "
United States
Tammy D.
The price is ￥28,253
￥35,473 total
includes taxes & fees
Mar 10 - Mar 11
Beautiful, Secluded & Private on 50-acre Estate
Smart TV

Apartment in Frederick

Pet-friendly, heart of downtown
10.0 out of 10, Exceptional, (8 reviews)
"Very convenient to everything. Quick walk to shops, breweries, and restaurants."
United States
JENNIFER
The price is ￥9,104
￥29,616 total
includes taxes & fees
Mar 23 - Mar 24
Pet-friendly, heart of downtown
Apartment (3 Bedrooms) | Front of property

Apartment in Frederick

2 Mi to Dtwn Frederick: Updated Townhome
4.0 star property
The price is ￥30,764
￥77,894 total
includes taxes & fees
Mar 7 - Mar 8
2 Mi to Dtwn Frederick: Updated Townhome
Exterior

Cabin in Shepherdstown

❤️ Secluded 1940s Romantic Tiny House on the River
9.8 out of 10, Exceptional, (72 reviews)
"This trip was to celebrate my 64th birthday and wind down from my busy job It was perfect for both .. very relaxing, and very cozy. We'd love to stay again."
United States
Kaleb C
The price is ￥10,736
￥21,503 total
includes taxes & fees
Mar 12 - Mar 13
❤️ Secluded 1940s Romantic Tiny House on the River
TV, fireplace

Cabin in Keedysville

Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
9.8 out of 10, Exceptional, (67 reviews)
"Great stay! We would book again. "
United States
Sam F.
The price is ￥17,644
￥60,032 total
includes taxes & fees
Mar 8 - Mar 9
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
Interior

Cottage in Hamilton

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
9.8 out of 10, Exceptional, (12 reviews)
"Absolutely amazing place and stay! I could not possibly be more impressed and I look forward to coming back."
United States
Jasmine M.
The price is ￥35,316
￥61,555 total
includes taxes & fees
Mar 7 - Mar 8
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Casino

Vacation Home in Sharpsburg

5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ Fire Pit
10.0 out of 10, Exceptional, (42 reviews)
"We had an amazing time - lots of walks and places to see - very historical - winery right next door which was an added bonus - accommodation was everything we needed and more - look out for a friendly cat that paid a few visits - thank you Jordan for a great time and will definitely come back to the area"
United Kingdom
Jo W.
5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ Fire Pit
Fridge, microwave, oven, stovetop

Vacation Home in Frederick

Newly constructed 6 bedroom home
10.0 out of 10, Exceptional, (14 reviews)
"Quiet and convenient stay in very comfortable house. Host was on top of every question and very helpful, answered questions immediately. Many thanks for a lovely stay."
United States
Janine S.
The price is ￥33,432
￥73,039 total
includes taxes & fees
Mar 8 - Mar 9
Newly constructed 6 bedroom home
Microwave, oven, stovetop, dishwasher

Vacation Home in Rohrersville

Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
10.0 out of 10, Exceptional, (7 reviews)
"The hosts were easy to work with. The house was need and clean! Great experience!"
United States
Chad S.
The price is ￥39,385
￥66,797 total
includes taxes & fees
Mar 13 - Mar 14
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
Property grounds

Apartment in Hagerstown

Galloping Getaway on the rolling hills of GemStone Stable
10.0 out of 10, Exceptional, (17 reviews)
"Perfect for us as we visited family."
United States
Felicia H.
The price is ￥19,620
￥29,697 total
includes taxes & fees
Mar 18 - Mar 19
Galloping Getaway on the rolling hills of GemStone Stable
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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Top Middletown Hotel Reviews

Best Western Leesburg Hotel & Conference Center

Best Western Leesburg Hotel & Conference Center

6/10 Okay
"Safe but no hot water. "
Deborah 1-night trip
Posted 7 hours ago
Best Western Leesburg Hotel & Conference Center

Find out more about Middletown

Search for holiday rentals in Middletown on Expedia! You can easily find your home rentals, villas, holiday apartments in Middletown using one of the methods below:

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Look no further and take a look at our great range of rental properties in Middletown!

Frequently asked questions

Can I find a vacation rental in Middletown?

Yes, we offer vacation rentals near well known points of interest in Middletown, or you can select a secluded option if you're looking for relaxation. 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's the top vacation rental in Middletown?

Riverside cottage, minutes from historic Harpers Ferry! Private river access!: This vacation home near Middletown offers a fireplace, a balcony, and a barbecue grill 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 vacation with amenities like a selection of games.

How many vacation rentals will I find in Middletown?

Expedia has 6 vacation rentals for your stay in Middletown.

What can I see and do in Middletown?

While exploring the area, visit family-friendly sights like Catoctin Wildlife Preserve and Zoo, or get outside and enjoy nature at Baker Park. Other places in town to visit include Maryland National Golf Club and Gambrill State Park.

What are vacation rentals like in Middletown?

Vacation rentals are private accommodations you can book for a couple days or more in Middletown. Vacation rentals offer extras like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for a small group gathering.