Middletown Vacation Rentals

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Our top choices for Middletown vacation rentals

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (140)
"Love the place will book again"
United States
WAYNE M.
$230 nightly
The price is $244
Jan 4 - Jan 5, 2026
Total with taxes and fees
Charming "Cream of the Crop" Cape ~❤️of Middletown

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, (110)
"I’ve stayed here and will absolutely stay again."
United States
Katherine M.
$182 nightly
The price is $193
Jan 5 - Jan 6, 2026
Total with taxes and fees
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

*Modern Condo In Downtown Frederick*

*Modern Condo In Downtown Frederick*
Downtown Frederick
9.2 out of 10, Wonderful, (76)
"Great location and has exactly what you need to enjoy a stay in downtown Frederick!"
United States
Amy R.
$248 nightly
The price is $263
Jan 3 - Jan 4, 2026
Total with taxes and fees
*Modern Condo In Downtown Frederick*

Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.

Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.
Blue Ridge Summit
9.4 out of 10, Exceptional, (11)
"Great spot close to the wedding venue!!"
United States
Alfred T.
$161 nightly
The price is $178
Jan 1 - Jan 2, 2026
Total with taxes and fees
Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.

Cozy Getaway near Harper`s Ferry, C&O & Potomac

Cozy Getaway near Harper`s Ferry, C&O & Potomac
Brunswick
9.8 out of 10, Exceptional, (54)
"Great little apartment, great value, walking distance to trail and right in town!"
United States
Jess A.
$160 nightly
The price is $170
Jan 1 - Jan 2, 2026
Total with taxes and fees
Cozy Getaway near Harper`s Ferry, C&O & Potomac

Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home

Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home
Myersville
9.4 out of 10, Exceptional, (111)
"Alot of choices for food and snacks within walking distance. "
United States
Cherilyn H.
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home

Rebels Rest - Cabin with Enchanting Sunset Views!

Rebels Rest - Cabin with Enchanting Sunset Views!
Harpers Ferry
9.8 out of 10, Exceptional, (31)
"Would come back anytime, very scenic and easy check-in process"
United States
Mark F.
$340 nightly
The price is $378
Jan 5 - Jan 6, 2026
Total with taxes and fees
Rebels Rest - Cabin with Enchanting Sunset Views!

Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Jefferson
9.8 out of 10, Exceptional, (58)
"Very conveniently located for our visit with an amazing bakery and awesome meat market across the street. "
United States
Kathryn B.
$236 nightly
The price is $250
Jan 4 - Jan 5, 2026
Total with taxes and fees
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

Blue Ridge Getaway - Sunset Views, A.T. Access

Blue Ridge Getaway - Sunset Views, A.T. Access
Harpers Ferry
9.8 out of 10, Exceptional, (64)
"Comfortable, clean, welcoming, wonderful hot tub, great view from the porch!"
United States
Carol M.
$328 nightly
The price is $365
Jan 7 - Jan 8, 2026
Total with taxes and fees
Blue Ridge Getaway - Sunset Views, A.T. Access

Cozy Mountain Cabin w/ Steam Shower. Family Friendly!

Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
Harpers Ferry
10.0 out of 10, Exceptional, (83)
"This is a super cute mountain cabin that has been completely redone with some pretty high end finishes. Our family thoroughly enjoyed our quick visit!"
United States
Sara S.
$257 nightly
The price is $286
Jan 6 - Jan 7, 2026
Total with taxes and fees
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (67)
"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
$95 nightly
The price is $105
Jan 12 - Jan 13, 2026
Total with taxes and fees
❤️ Secluded 1940s Romantic Tiny House on the River

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Downtown Frederick
9.4 out of 10, Exceptional, (120)
"Excellent location for our family wedding weekend! We walked to all the events of the weekend."
United States
Cynthia L.
$297 nightly
The price is $315
Jan 11 - Jan 12, 2026
Total with taxes and fees
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

Newly constructed 6 bedroom home

Newly constructed 6 bedroom home
Frederick
10.0 out of 10, Exceptional, (14)
"This is our second time staying here and we really love how easily we all fit in. It's clean, family friendly, and have lots of space."
United States
Bonnie S.
$438 nightly
The price is $464
Jan 1 - Jan 2, 2026
Total with taxes and fees
Newly constructed 6 bedroom home

Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.4 out of 10, Exceptional, (87)
"I loved the trip to that cabin, one of the most wonderful things"
United States
Roberto R.
$298 nightly
The price is $316
Jan 4 - Jan 5, 2026
Total with taxes and fees
Antietam Creek - Quiet 2 Bedroom Cabin

Enchanting Cottage, walk to Downtown Harpers Ferry

Enchanting Cottage, walk to Downtown Harpers Ferry
Harpers Ferry
9.6 out of 10, Exceptional, (44)
"We really enjoyed our stay here, the location is perfect for exploring Harpers Ferry, within walking distance to everything. The cottage is well equipped, clean and cozy, perfect for a couples get away, would book again if returning to HF. The owner was very communicated, had well organized info for the stay and was easy to work with"
United States
Brandon L.
$254 nightly
The price is $266
Jan 19 - Jan 20, 2026
Total with taxes and fees
Enchanting Cottage, walk to Downtown Harpers Ferry

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

Secluded Cabin a Stone's Throw From the A.T.!
Harpers Ferry
10.0 out of 10, Exceptional, (34)
"Great property to stay at. Very comfortable, quiet, and secluded. Would recommend this property to anyone. "
United States
Leonardf B.
$351 nightly
The price is $391
Jan 8 - Jan 9, 2026
Total with taxes and fees
Secluded Cabin a Stone's Throw From the A.T.!

Cozy Cabin Hidden Away on a Lake!

Cozy Cabin Hidden Away on a Lake!
Harpers Ferry
9.6 out of 10, Exceptional, (44)
"The house and setting were perfect. We recommend the cabin."
United States
Pat A.
$336 nightly
The price is $374
Jan 8 - Jan 9, 2026
Total with taxes and fees
Cozy Cabin Hidden Away on a Lake!

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

Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
Keedysville
9.8 out of 10, Exceptional, (65)
"Great stay! We would book again. "
United States
Sam F.
$328 nightly
The price is $365
Jan 6 - Jan 7, 2026
Total with taxes and fees
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

Beautiful, Historic, Hiking, Biking and C&O Canal

Beautiful, Historic, Hiking, Biking and C&O Canal
Brunswick
10.0 out of 10, Exceptional, (22)
"For visiting Harpers Ferry, location was ideal."
United States
Barbara W.
$188 nightly
The price is $199
Jan 3 - Jan 4, 2026
Total with taxes and fees
Beautiful, Historic, Hiking, Biking and C&O Canal

Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (26)
"Clean, great location, friendly owner"
United States
Christian M.
$179 nightly
The price is $190
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cozy, dog-friendly, downtown
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

Everything you need to know about Middletown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middletown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middletown vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middletown. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Middletown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $105 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Middletown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middletown vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middletown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Hot tub, Campfire ring and great location!: This vacation home rental near Middletown is located on a river and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a hot tub.

How many vacation rentals will I find in Middletown?

Expedia has 5 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 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.