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
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

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, (152 reviews)
"An absolutely charming getaway spot tucked in a small town with trendy shops and eateries. Our host gave fabulous recommendations and the property was spotless, cozy and well equipped for the perfect weekend getaway."
United States
Jennifer P.
$229 nightly
The price is $243
Aug 6 - Aug 7
Total with taxes and fees
Charming "Cream of the Crop" Cape ~❤️of Middletown
Exterior

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

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (81 reviews)
"Enjoyed my stay I appreciate the view and Rich. "
United States
Joseph
$127 nightly
The price is $141
Aug 31 - Sep 1
Total with taxes and fees
❤️ Secluded 1940s Romantic Tiny House on the River
1 bedroom, WiFi (free), bed sheets

3. Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (35 reviews)
"Great location, clean place. "
United States
Warren B.
$196 nightly
The price is $208
Aug 10 - Aug 11
Total with taxes and fees
Cozy, dog-friendly, downtown
Exterior detail

4. Huge 1br apt, baby-friendly, dogs, walkable downtown

Huge 1br apt, baby-friendly, dogs, walkable downtown
Downtown Frederick
10.0 out of 10, Exceptional, (10 reviews)
"Great location for a peaceful solo night away -- thanks!"
United States
Kristina S.
$202 nightly
The price is $214
Aug 31 - Sep 1
Total with taxes and fees
Huge 1br apt, baby-friendly, dogs, walkable downtown
Coffee/tea maker, fridge, microwave, oven

5. 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, (69 reviews)
"Lovely home. Great location! Host was amazingly helpful!"
United States
Tory D.
$271 nightly
The price is $287
Aug 9 - Aug 10
Total with taxes and fees
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Exterior

6. 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, (65 reviews)
"The apartment was cozy and just as described. Check-in was super easy and the owners were very responsive to any questions we had. Thanks for a super pleasant stay!"
United States
Candi M.
$169 nightly
The price is $179
Aug 6 - Aug 7
Total with taxes and fees
Cozy Getaway near Harper`s Ferry, C&O & Potomac
Exterior

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

Beautiful, Historic, Hiking, Biking and C&O Canal
Brunswick
10.0 out of 10, Exceptional, (26 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.
$186 nightly
The price is $197
Aug 12 - Aug 13
Total with taxes and fees
Beautiful, Historic, Hiking, Biking and C&O Canal
Smart TV

8. Pet-friendly, heart of downtown

Pet-friendly, heart of downtown
Frederick
10.0 out of 10, Exceptional, (9 reviews)
"This was a great property in an excellent location! Communication was great and the whole process was seamless. "
United States
nikki b.
$193 nightly
The price is $205
Aug 31 - Sep 1
Total with taxes and fees
Pet-friendly, heart of downtown
Interior

9. Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (95 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
Aug 6 - Aug 7
Total with taxes and fees
Antietam Creek - Quiet 2 Bedroom Cabin
A park with a pond, a bridge, and a church in the background.

10. 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, (133 reviews)
"The place was so fun and close to the bars! The rooms where cleans "
United States
Anonymous traveler
$273 nightly
The price is $289
Aug 9 - Aug 10
Total with taxes and fees
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Outdoor dining

11. Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick

Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Frederick
9.8 out of 10, Exceptional, (50 reviews)
"Great location--easy walk to downtown Frederick. Comfortable beds, pleasant spaces and light."
United States
Alan S.
$254 nightly
The price is $269
Aug 31 - Sep 1
Total with taxes and fees
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Coffee/tea maker, fridge, microwave, oven

12. Modern Condo Right off Market Street

Modern Condo Right off Market Street
Downtown Frederick
9.2 out of 10, Wonderful, (101 reviews)
"Great place to stay. It was close to the park. It is a beautiful clean place. "
United States
Kimberly & Randy H.
$322 nightly
The price is $341
Aug 17 - Aug 18
Total with taxes and fees
Modern Condo Right off Market Street
Coffee/tea maker, fridge, microwave, oven

13. 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.
$251 nightly
The price is $266
Aug 12 - Aug 13
Total with taxes and fees
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Microwave, oven, stovetop, dishwasher

14. 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, (14 reviews)
"Beautiful historic home. Hosts were very welcoming and the place was newly renovated. "
United States
Drew M.
$429 nightly
The price is $455
Aug 12 - Aug 13
Total with taxes and fees
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
Exterior

15. 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, (209 reviews)
"Great place, pet friendly. "
United States
Doug P.
$165 nightly
The price is $175
Aug 22 - Aug 23
Total with taxes and fees
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Dining

16. 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.
$333 nightly
The price is $353
Aug 17 - Aug 18
Total with taxes and fees
Luxury Condo In Downtown Frederick
TV, fireplace

17. 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, (70 reviews)
"Beautiful cabin in the forest especially in the evening when the fire flies out and the sun sets."
United States
Jared
$365 nightly
The price is $406
Aug 12 - Aug 13
Total with taxes and fees
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
Exterior detail

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

Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.
Blue Ridge Summit
9.6 out of 10, Exceptional, (19 reviews)
"Location and amenities"
United States
Shane B.
$182 nightly
The price is $201
Aug 10 - Aug 11
Total with taxes and fees
Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.
Outdoor dining

19. Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach

Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
Harpers Ferry
9.8 out of 10, Exceptional, (9 reviews)
"A wonderfully equipped home in a lovely location. Everything you could ever need was on hand. "
United States
alison m.
$376 nightly
The price is $418
Sep 3 - Sep 4
Total with taxes and fees
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
Exterior

20. 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, (8 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.
$236 nightly
The price is $250
Aug 10 - Aug 11
Total with taxes and fees
Historic Getaway near C&O Canal, hiking and biking
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

Country Inn & Suites by Radisson, Hagerstown, MD

Country Inn & Suites by Radisson, Hagerstown, MD

10/10 Excellent
"Beautiful hotel, great food and friendly staffs."
Jeny 1-night trip
Posted 8 hours ago
Country Inn & Suites by Radisson, Hagerstown, MD

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 $141 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?

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 Orchid Cellar Winery and Maryland National Golf Club.

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.