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Middletown Holiday Rentals

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Our top choices for Middletown holiday rentals

9.6 out of 10, Exceptional, (110 reviews)
"I’ve stayed here and will absolutely stay again."
United States
Katherine M.
The price is NZ$316
includes taxes & fees
12 Jan - 13 Jan
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
10.0 out of 10, Exceptional, (141 reviews)
"Love the place will book again"
United States
WAYNE M.
The price is NZ$411
includes taxes & fees
15 Jan - 16 Jan
Charming "Cream of the Crop" Cape ~❤️of Middletown
9.8 out of 10, Exceptional, (69 reviews)
"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
The price is NZ$183
includes taxes & fees
19 Jan - 20 Jan
❤️ Secluded 1940s Romantic Tiny House on the River

Apartment in Frederick

Pet-friendly, heart of downtown
10.0 out of 10, Exceptional, (8 reviews)
"Very convenient to everything. Quick walk to shops, breweries, and restaurants."
United States
JENNIFER
The price is NZ$327
includes taxes & fees
12 Jan - 13 Jan
Pet-friendly, heart of downtown

Apartment in Frederick

Cozy, dog-friendly, downtown
10.0 out of 10, Exceptional, (26 reviews)
"Clean, great location, friendly owner"
United States
Christian M.
The price is NZ$344
includes taxes & fees
1 Feb - 2 Feb
Cozy, dog-friendly, downtown
10.0 out of 10, Exceptional, (9 reviews)
"Cute little house that my husband and I enjoyed for the weekend. Great location close to Martinsburg. It had everything we needed for our weekend The host communicated well, we had no issues, and we would definitely stay here again. Thank you!"
United States
Jennifer E.
The price is NZ$281
includes taxes & fees
12 Jan - 13 Jan
Bring Your Own Boat - Meticulously restored house on the Potomac River

Apartment in Frederick

Cozy Pine Tree Nest
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.
The price is NZ$296
includes taxes & fees
18 Jan - 19 Jan
Cozy Pine Tree Nest
10.0 out of 10, Exceptional, (6 reviews)
"Amazing stay love this place very cozy house ."
United States
Aimee C.
The price is NZ$341
includes taxes & fees
13 Jan - 14 Jan
Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown
10.0 out of 10, Exceptional, (83 reviews)
"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.
The price is NZ$476
includes taxes & fees
13 Jan - 14 Jan
Cozy Mountain Cabin w/ Steam Shower! Family Friendly.
2.0 star property
9.8 out of 10, Exceptional, (8 reviews)
"We stayed here for our honeymoon and it was very nice and peaceful "
United States
Robert F.
The price is NZ$656
includes taxes & fees
19 Jan - 20 Jan
Aslan's How - Cabin with Valley Views & Hot Tub!
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"The home was perfect for our visit.We were in and out all weekend but really appreciated the well stocked kitchen supplies, the comfortable beds and the hot water levels. We were able to relax in the spacious living room and spend some time on the little outdoor areas. We would stay again but if the group was much bigger there may be issues as there are only bathrooms on the first floor. "
United States
Erin J.
The price is NZ$623
includes taxes & fees
15 Jan - 16 Jan
New, Contemporary House in Historic Harpers Ferry
2.0 star property
9.8 out of 10, Exceptional, (14 reviews)
"Everything was great! We had a lovely stay."
United States
Beth D.
The price is NZ$606
includes taxes & fees
19 Jan - 20 Jan
Log Cabin w/ Hot Tub & Waterfront Patio!
10.0 out of 10, Exceptional, (16 reviews)
"Great location. Great house. Could not have asked for more. "
United States
A. Bland and D. T.
The price is NZ$674
includes taxes & fees
15 Jan - 16 Jan
Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
9.8 out of 10, Exceptional, (43 reviews)
"The place was super cute and clean. It was the perfect little getaway spot for my husband and I’s anniversary. "
United States
Holly W.
The price is NZ$297
includes taxes & fees
12 Jan - 13 Jan
The Carriage House at Carrot Top Cottage
9.8 out of 10, Exceptional, (54 reviews)
"Great little apartment, great value, walking distance to trail and right in town!"
United States
Jess A.
The price is NZ$296
includes taxes & fees
18 Jan - 19 Jan
Cozy Getaway near Harper`s Ferry, C&O & Potomac
9.8 out of 10, Exceptional, (92 reviews)
"The Toll House was clean, had all the amenities advertised, and host had great communication. Very nice to have a fenced yard for my small dog to roam. I recommend this to others! "
United States
Sharon
The price is NZ$391
includes taxes & fees
12 Jan - 13 Jan
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
9.8 out of 10, Exceptional, (58 reviews)
"Great house to use during our visit to Jefferson. Kitchen is well equipped, and coffee supplies are provided. Comfy beds plus air conditioning made for great sleep. "
United States
Kathryn B.
The price is NZ$494
includes taxes & fees
17 Jan - 18 Jan
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

Holiday Home in Downtown Frederick

*Luxury Condo In Downtown Frederick*
9.0 out of 10, Wonderful, (72 reviews)
"Great time. Everything was perfect and place was just what we needed. "
United States
dominick c.
The price is NZ$457
includes taxes & fees
12 Jan - 13 Jan
*Luxury Condo In Downtown Frederick*
9.8 out of 10, Exceptional, (19 reviews)
"Was wonderful..private and peaceful. Perfect getaway. "
United States
Courtney G.
The price is NZ$265
includes taxes & fees
19 Jan - 20 Jan
Birch Cabin at Hunting Creek Hideaway
9.8 out of 10, Exceptional, (31 reviews)
"Beautiful Sunsets, older cabin, not too steep of a drive up, outside deck is nice and fire pit area out front! Harper’s Ferry Area is cute and full of history! Be in shape to hike and climb while you are here, especially if you plan on doing a ghost walk after walking the town all day! 5 friends girls trip was great! "
United States
Teresa R.
The price is NZ$653
includes taxes & fees
15 Jan - 16 Jan
Rebels Rest - Cabin with Enchanting Sunset Views!
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Middletown holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middletown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middletown holiday rentals we have selected for you start as low as NZ$183 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown holiday 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 holiday.

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 holiday rental in Middletown?

Yes, there are holiday rentals close to the most popular sights in Middletown, or you can select a more secluded option if you're looking for a relaxing stay. 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 are some of the best holiday rentals that Middletown has to offer?

1805 Farmhouse with Heated Pool in Harpers Ferry: This holiday home rental outside of Middletown is located in a rural location, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a full-sized fridge, a dishwasher and a stovetop, so that you can cook with friends or family. It offers a furnished patio, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Middletown?

Expedia has 5 holiday rentals for your stay in Middletown.

What can I see and do in Middletown?

While exploring the area, visit family-friendly sights like John Brown Wax Museum, or get outside and enjoy nature at Baker Park. Other places in town to visit include Maryland National Golf Club and Washington Monument State Park.

What are holiday rentals like in Middletown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middletown. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have everything you need. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.