A stone tower with a staircase leading up to it.

Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Middletown vacation rentals

Exterior

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (154 reviews)
"Great place to stay. Very clean and beautiful. The Host was very nice too and kept us informed. We will definetly stay there again!"
United States
Adair M.
$228 nightly
The price is $242
Sep 3 - Sep 4
Total with taxes and fees
Charming "Cream of the Crop" Cape ~❤️of Middletown
Living area

2. Cozy Downtown Cabin - Family Friendly

Cozy Downtown Cabin - Family Friendly
Middletown
$202 nightly
The price is $214
Sep 4 - Sep 5
Total with taxes and fees
Cozy Downtown Cabin - Family Friendly
Private kitchen

3. 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
10.0 out of 10, Exceptional, (72 reviews)
"Lovely home. Great location! Host was amazingly helpful!"
United States
Tory D.
$228 nightly
The price is $242
Sep 3 - Sep 4
Total with taxes and fees
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Room

4. Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (36 reviews)
"Great location, clean place. "
United States
Warren B.
$199 nightly
The price is $211
Sep 3 - Sep 4
Total with taxes and fees
Cozy, dog-friendly, downtown
Private kitchen

5. Patty's Place - Private and Convenient Apartment near Downtown

Patty's Place - Private and Convenient Apartment near Downtown
Frederick
10.0 out of 10, Exceptional, (17 reviews)
"Place was perfect and tbe location great. East in and out town..or to get to down town"
United States
Andrew
$199 nightly
The price is $211
Sep 6 - Sep 7
Total with taxes and fees
Patty's Place - Private and Convenient Apartment near Downtown
Dining

6. Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (97 reviews)
"Very clean, had everything we needed and close to shopping and restaurants. "
United States
Kathy S.
$330 nightly
The price is $350
Sep 7 - Sep 8
Total with taxes and fees
Luxury Condo In Downtown Frederick
Living area

7. Pet-friendly, heart of downtown

Pet-friendly, heart of downtown
Frederick
10.0 out of 10, Exceptional, (9 reviews)
"Great location. We did not bring a pet but they thoughtfully provided a dog bed for those who do, which was very cute. It was great that they provide dishes for use on property and the kitchen cabinets were well labelled. There is a good ice cream place a block away and it was quick and easy to walk to the major downtown areas. We would stay here again in the future"
United States
Erica B.
$198 nightly
The price is $210
Sep 30 - Oct 1
Total with taxes and fees
Pet-friendly, heart of downtown
Private kitchen

8. Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (69 reviews)
"Wonderfully remodeled spot, great amenities, extremely close to downtown, was perfect for our trip!"
United States
Andrew F.
$255 nightly
The price is $270
Sep 14 - Sep 15
Total with taxes and fees
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
A park with a pond, a bridge, and a church in the background.

9. 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, (136 reviews)
"Very old but lovely building. Great parking and patio."
United States
Jennifer W.
$276 nightly
The price is $293
Sep 6 - Sep 7
Total with taxes and fees
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Private kitchen

10. Modern Condo Right off Market Street

Modern Condo Right off Market Street
Downtown Frederick
9.2 out of 10, Wonderful, (102 reviews)
"Great place!"
United States
Danielle G.
$313 nightly
The price is $332
Sep 7 - Sep 8
Total with taxes and fees
Modern Condo Right off Market Street
Interior

11. Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (97 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
Sep 3 - Sep 4
Total with taxes and fees
Antietam Creek - Quiet 2 Bedroom Cabin
Exterior

12. 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, (67 reviews)
"Cute downtown area with multiple spots to grab breakfast and convenience store stuff. Easy access to Harper's Ferry and made for a nice restful spot between hikes in nature and around town."
United States
Robert
$169 nightly
The price is $179
Sep 3 - Sep 4
Total with taxes and fees
Cozy Getaway near Harper`s Ferry, C&O & Potomac
Living area

13. 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, (75 reviews)
"Beautiful cabin in the forest especially in the evening when the fire flies out and the sun sets."
United States
Jared
$346 nightly
The price is $385
Sep 10 - Sep 11
Total with taxes and fees
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
Exterior

14. ❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (83 reviews)
"Enjoyed my stay I appreciate the view and Rich. "
United States
Joseph
$120 nightly
The price is $133
Sep 14 - Sep 15
Total with taxes and fees
❤️ Secluded 1940s Romantic Tiny House on the River
Exterior

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

Beautiful, Historic, Hiking, Biking and C&O Canal
Brunswick
10.0 out of 10, Exceptional, (29 reviews)
"The host was extremely welcoming and kind to us. We spent a week here and loved our stay. We are so grateful to have been able to stay here with Kim and Todd. "
United States
Christina H.
$188 nightly
The price is $199
Sep 7 - Sep 8
Total with taxes and fees
Beautiful, Historic, Hiking, Biking and C&O Canal
Exterior

16. Historic Getaway near C&O Canal, hiking and biking

Historic Getaway near C&O Canal, hiking and biking
Brunswick
9.8 out of 10, Exceptional, (11 reviews)
"We had a great time. It was a great location to be close to the aid station for the C&O ultra. Great coffee shop nearby. It was comfortable and nice. Owners were very communicative."
United States
Angele C.
$234 nightly
The price is $248
Sep 3 - Sep 4
Total with taxes and fees
Historic Getaway near C&O Canal, hiking and biking
Interior

17. Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (44 reviews)
"Beautiful property and just as described and shown in the pictures. "
United States
Kent Y.
$331 nightly
The price is $369
Sep 22 - Sep 23
Total with taxes and fees
Antietam Look Out - Incredible Sunset Views!
Private kitchen

18. Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
Rohrersville
10.0 out of 10, Exceptional, (16 reviews)
"Great location for the Spring Festival. The beds were very comfortable. Kitchen was well equipped ."
United States
Renee W.
$429 nightly
The price is $455
Sep 9 - Sep 10
Total with taxes and fees
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
Dining

19. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (24 reviews)
"Host let us in a bit early which was nice!"
United States
John
$197 nightly
The price is $219
Sep 6 - Sep 7
Total with taxes and fees
Quaint Mini Cottage in Shepherdstown - Walking Distance
Exterior

20. 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, (210 reviews)
"Great place, pet friendly. "
United States
Doug P.
$165 nightly
The price is $175
Sep 7 - Sep 8
Total with taxes and fees
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
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

Quality Inn Harpers Ferry - Charles Town

Quality Inn Harpers Ferry - Charles Town

10/10 Excellent
"Staff very friendly. Room was clean just old looking. Breakfast is good. I would stay here again for sure."
Jeffrey 1-night trip
Posted less than an hour ago
Quality Inn Harpers Ferry - Charles Town

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 $133 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.

Explore a world of travel with Expedia

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?

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.: This vacation home rental near Middletown is located in the city center and has a fireplace, a balcony, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. 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 7 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 Washington Monument 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.