Middletown Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

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, (114 reviews)
"Good stay. Would visit again. "
United States
Lonnie F.
$192 nightly
The price is $204
May 10 - May 11
Total with taxes and fees
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, (145 reviews)
"Love the place will book again"
United States
WAYNE M.
$243 nightly
The price is $258
May 10 - May 11
Total with taxes and fees
Charming "Cream of the Crop" Cape ~❤️of Middletown

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (74 reviews)
"Cozy home, great location, and kind and helpful host. Would like to stay again. "
United States
Matthew S.
$122 nightly
The price is $135
May 19 - May 20
Total with taxes and fees
❤️ Secluded 1940s Romantic Tiny House on the River

Cabin at the Gap | You Won't Believe the View!

Cabin at the Gap | You Won't Believe the View!
Harpers Ferry
$306 nightly
The price is $341
May 10 - May 11
Total with taxes and fees
Cabin at the Gap | You Won't Believe the View!

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

Rural & Historic Detour Escape w/ Horses On-site!
3.0 star property
Keymar
$407 nightly
The price is $432
May 8 - May 9
Total with taxes and fees
Rural & Historic Detour Escape w/ Horses On-site!

Antietam Toll House~ an historic waterfront cabin with fully fenced yard.

Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
Waynesboro
9.8 out of 10, Exceptional, (100 reviews)
"Beautiful location! The host was extremely responsive with any questions most texts were returned within minutes! Will definitely stay here again. "
United States
Michael R.
$219 nightly
The price is $242
May 10 - May 11
Total with taxes and fees
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.

Cozy Pine Tree Nest

Cozy Pine Tree Nest
Frederick
9.4 out of 10, Exceptional, (11 reviews)
"Peaceful studio with a lovely view off the porch. Was easy to find and all aspects of the stay were smooth. Perfect place for a few days in Frederick "
United States
Morgan P.
$160 nightly
The price is $170
May 9 - May 10
Total with taxes and fees
Cozy Pine Tree Nest

Bring Your Own Boat - Meticulously restored house on the Potomac River

Bring Your Own Boat - Meticulously restored house on the Potomac River
Hedgesville
9.6 out of 10, Exceptional, (10 reviews)
"Our stay was amazing and we really enjoyed ourselves. The place was perfect and quiet and peaceful! We will be booking with them again! "
United States
Kyndal B.
$169 nightly
The price is $188
May 7 - May 8
Total with taxes and fees
Bring Your Own Boat - Meticulously restored house on the Potomac River

~Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake!

~Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake!
Harpers Ferry
10.0 out of 10, Exceptional, (88 reviews)
"The host had great communication and the place was exactly as pictured! "
United States
Colleen J.
$298 nightly
The price is $332
May 7 - May 8
Total with taxes and fees
~Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake!

Birch Cabin at Hunting Creek Hideaway

Birch Cabin at Hunting Creek Hideaway
Thurmont
9.8 out of 10, Exceptional, (27 reviews)
"We had a very nice stay here, kitchen and bathroom had all necessary amenities provided. Cozy cabin, a little chilly at night but blankets were provided as well so it was OK."
United States
Emily Z.
$136 nightly
The price is $144
May 11 - May 12
Total with taxes and fees
Birch Cabin at Hunting Creek Hideaway

Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (89 reviews)
"Did a small girls night here and we had the best time! Out there and quiet for a get away and plenty to do inside for colder weather we loved the bookshelf full of board games and books and the piano to tinker around on! The gas fireplace kept the whole place cranking with heat no problems Definitely would stay here again!"
United States
Kandy T.
$310 nightly
The price is $329
May 7 - May 8
Total with taxes and fees
Antietam Creek - Quiet 2 Bedroom Cabin

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, (62 reviews)
"The beds were incredibly comfortable. Great house. Great location. "
United States
Julie B.
$220 nightly
The price is $233
May 7 - May 8
Total with taxes and fees
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

Cottage w/ Hot Tub and 100-Mile Valley Views!

Cottage w/ Hot Tub and 100-Mile Valley Views!
Harpers Ferry
9.8 out of 10, Exceptional, (21 reviews)
"Great view, very secluded"
United States
Matt s.
$340 nightly
The price is $378
May 11 - May 12
Total with taxes and fees
Cottage w/ Hot Tub and 100-Mile Valley Views!

Cozy cabin w/hot tub & game room

Cozy cabin w/hot tub & game room
Harpers Ferry
9.0 out of 10, Wonderful, (65 reviews)
"House was wonderful, and I loved how often Tony checked in! Will absolutely be staying here again!"
United States
Chelsey-Ann
$309 nightly
The price is $322
May 11 - May 12
Total with taxes and fees
Cozy cabin w/hot tub & game room

Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (28 reviews)
"Great location, clean place. "
United States
Warren B.
$190 nightly
The price is $202
May 11 - May 12
Total with taxes and fees
Cozy, dog-friendly, downtown

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Sharpsburg
9.6 out of 10, Exceptional, (200 reviews)
"We enjoyed our stay and the location was excellent"
United States
Barbara W.
$165 nightly
The price is $175
May 10 - May 11
Total with taxes and fees
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (87 reviews)
"Great location and very comfortable. Definitely will consider for future trips to this area."
United States
Jon E.
$312 nightly
The price is $331
May 7 - May 8
Total with taxes and fees
Luxury Condo In Downtown Frederick

Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (36 reviews)
"Great communication, very clean, beautiful views!"
United States
Lorie K.
$318 nightly
The price is $354
May 7 - May 8
Total with taxes and fees
Antietam Look Out - Incredible Sunset Views!

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, (67 reviews)
"Great home "
United States
January D.
$340 nightly
The price is $379
May 13 - May 14
Total with taxes and fees
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

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.
$199 nightly
The price is $211
May 18 - May 19
Total with taxes and fees
Pet-friendly, heart of 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.
Save an average of 15% on thousands of hotels when you're signed in

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 $135 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?

Walk to Harpers Ferry! Dog-friendly. Beautiful Views.: This vacation home rental near Middletown offers a patio, a selection of games, and a barbecue grill to help you feel perfectly comfortable 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.

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.