Middletown Vacation Rentals

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Our top choices for Middletown vacation rentals

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Middletown
9.6 out of 10, Exceptional, (111 reviews)
"Cozy & dog friendly "
United States
Lauren F.
The price is CA $172
CA $348 total
includes taxes & fees
Apr 1 - Apr 2
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (143 reviews)
"Love the place will book again"
United States
WAYNE M.
The price is CA $124
CA $332 total
includes taxes & fees
Mar 26 - Mar 27
Charming "Cream of the Crop" Cape ~❤️of Middletown

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (65 reviews)
"Great kitchen, very comfortable beds. Well air conditioned."
United States
Whitney C.
The price is CA $179
CA $382 total
includes taxes & fees
Apr 6 - Apr 7
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Rural & Historic Detour Escape w/ Horses On-site!

Rural & Historic Detour Escape w/ Horses On-site!
3.0 star property
Keymar
The price is CA $185
CA $592 total
includes taxes & fees
Mar 25 - Mar 26
Rural & Historic Detour Escape w/ Horses On-site!

Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI

Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
Harpers Ferry
9.2 out of 10, Wonderful, (32 reviews)
"Enjoyed the levels, hot tub, porch to get outside with my coffee, pet strolling area marvelous and washer/dryer."
United States
tracey b.
The price is CA $273
CA $470 total
includes taxes & fees
Mar 26 - Mar 27
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI

Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
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 CA $274
CA $458 total
includes taxes & fees
Mar 25 - Mar 26
Antietam Creek - Quiet 2 Bedroom Cabin

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Hamilton
9.8 out of 10, Exceptional, (13 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 CA $309
CA $546 total
includes taxes & fees
Apr 5 - Apr 6
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

Newly constructed 6 bedroom home

Newly constructed 6 bedroom home
Frederick
10.0 out of 10, Exceptional, (15 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 CA $292
CA $643 total
includes taxes & fees
Mar 26 - Mar 27
Newly constructed 6 bedroom home

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

Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg
Fairfield
9.8 out of 10, Exceptional, (51 reviews)
"Everything was perfect. The property is very cute and comfortable and the host was wonderful!"
United States
Carey K.
The price is CA $494
CA $789 total
includes taxes & fees
Mar 25 - Mar 26
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg

Leesburg Hideaway- King Bed + Private Backyard

Leesburg Hideaway- King Bed + Private Backyard
Leesburg
10.0 out of 10, Exceptional, (33 reviews)
"Lovely property, really nicely furnished and clean. Brilliant location for lots of places locally and close enough to walk into Leesburg itself to get ice cream!"
United Kingdom
Rachael B.
The price is CA $185
CA $423 total
includes taxes & fees
Mar 29 - Mar 30
Leesburg Hideaway- King Bed + Private Backyard

Exclusive Wooded Chalet w Magnificent River Views

Exclusive Wooded Chalet w Magnificent River Views
Shepherdstown
10.0 out of 10, Exceptional, (16 reviews)
"Beautiful views "
United States
Darryl L.
The price is CA $350
CA $651 total
includes taxes & fees
Mar 25 - Mar 26
Exclusive Wooded Chalet w Magnificent River Views

Quaint Royal Cottage @ Historic Leesburg

Quaint Royal Cottage @ Historic Leesburg
Leesburg's Old and Historic District
10.0 out of 10, Exceptional, (10 reviews)
"Great location in a great town!"
United States
Gigi D.
Quaint Royal Cottage @ Historic Leesburg

Loft Apt Just off C&O near Harpers Ferry and AT

Loft Apt Just off C&O near Harpers Ferry and AT
Brunswick
10.0 out of 10, Exceptional, (18 reviews)
"Our Hosts were wonderful and the space was great. It sits right off of the bike trail and across the street from a great bakery and bike shop. We thoroughly enjoyed our stay."
United States
Mark B.
The price is CA $148
CA $279 total
includes taxes & fees
Apr 5 - Apr 6
Loft Apt Just off C&O near Harpers Ferry and AT

Mountain Retreat w/2 Living Spaces, Hot Tub & Deck

Mountain Retreat w/2 Living Spaces, Hot Tub & Deck
Harpers Ferry
The price is CA $221
CA $457 total
includes taxes & fees
Mar 25 - Mar 26
Mountain Retreat w/2 Living Spaces, Hot Tub & Deck

Pet-friendly, heart of downtown

Pet-friendly, heart of downtown
Frederick
10.0 out of 10, Exceptional, (8 reviews)
"This was a great property in an excellent location! Communication was great and the whole process was seamless. "
United States
nikki b.
The price is CA $80
CA $261 total
includes taxes & fees
Mar 31 - Apr 1
Pet-friendly, heart of downtown

Amazing dog-friendly cottage. Walk 2 Harpers Ferry

Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Harpers Ferry
9.8 out of 10, Exceptional, (24 reviews)
"Great house and location! "
United States
Johanna S.
The price is CA $254
CA $454 total
includes taxes & fees
Mar 26 - Mar 27
Amazing dog-friendly cottage. Walk 2 Harpers Ferry

Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (28 reviews)
"Clean, great location, friendly owner"
United States
Christian M.
The price is CA $82
CA $262 total
includes taxes & fees
Mar 31 - Apr 1
Cozy, dog-friendly, downtown

Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV

Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV
Harpers Ferry
10.0 out of 10, Exceptional, (7 reviews)
"Perfect place to spend a few nights with our two dogs. Very clean, great amenities, and beautifully decorated. Highly recommend!! "
United States
Megan L.
The price is CA $264
CA $634 total
includes taxes & fees
Mar 25 - Mar 26
Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV

A peaceful, forest retreat with stunning views near historic Harpers Ferry.

A peaceful, forest retreat with stunning views near historic Harpers Ferry.
Harpers Ferry
9.8 out of 10, Exceptional, (6 reviews)
"Great place to stay!! Very happy with the accommodations "
United States
Amanda E.
The price is CA $247
CA $533 total
includes taxes & fees
Mar 25 - Mar 26
A peaceful, forest retreat with stunning views near historic Harpers Ferry.

Birch Cabin at Hunting Creek Hideaway

Birch Cabin at Hunting Creek Hideaway
Thurmont
10.0 out of 10, Exceptional, (23 reviews)
"Beautiful location. Just what we were looking for."
United States
tony l.
The price is CA $128
CA $202 total
includes taxes & fees
Mar 31 - Apr 1
Birch Cabin at Hunting Creek Hideaway
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

Find out more about Middletown

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Middletown. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 rental 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 Gambrill State Park and South Mountain 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.