Middletown Holiday Rentals

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Our top choices for Middletown holiday rentals

9.6 out of 10, Exceptional, (111 reviews)
"I’ve stayed here and will absolutely stay again."
United States
Katherine M.
The price is AU$272
includes taxes & fees
15 Jan - 16 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 AU$476
includes taxes & fees
18 Jan - 19 Jan
Charming "Cream of the Crop" Cape ~❤️of Middletown
9.8 out of 10, Exceptional, (70 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 AU$159
includes taxes & fees
20 Jan - 21 Jan
❤️ Secluded 1940s Romantic Tiny House on the River
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 AU$243
includes taxes & fees
14 Jan - 15 Jan
Bring Your Own Boat - Meticulously restored house on the Potomac 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 AU$283
includes taxes & fees
19 Jan - 20 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 AU$290
includes taxes & fees
19 Jan - 20 Jan
Cozy, dog-friendly, downtown
10.0 out of 10, Exceptional, (6 reviews)
"Amazing stay love this place very cozy house ."
United States
Aimee C.
The price is AU$322
includes taxes & fees
19 Jan - 20 Jan
Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown
10.0 out of 10, Exceptional, (62 reviews)
"Always clean and comfortable home. Close to restaurants and shops but in quiet neighborhood to relax. Our second stay in this home. "
United States
Jelinda C.
The price is AU$392
includes taxes & fees
19 Jan - 20 Jan
Beautiful Remodeled Downtown Frederick Cottage (Pet-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 AU$560
includes taxes & fees
19 Jan - 20 Jan
Aslan's How - Cabin with Valley Views & Hot Tub!

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 AU$256
includes taxes & fees
15 Jan - 16 Jan
Cozy Pine Tree Nest
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 AU$533
includes taxes & fees
19 Jan - 20 Jan
Log Cabin w/ Hot Tub & Waterfront Patio!
9.8 out of 10, Exceptional, (19 reviews)
"It was a fabulous stay, and Brittany, the host, was very helpful with bringing a gas grill, AC, and communication. The scenery is very beautiful and it's very quiet. Great place for a hiking getaway."
United States
Fr. Andrew H.
The price is AU$229
includes taxes & fees
19 Jan - 20 Jan
Birch Cabin at Hunting Creek Hideaway
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 AU$338
includes taxes & fees
14 Jan - 15 Jan
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
9.8 out of 10, Exceptional, (66 reviews)
"Great stay! We would book again. "
United States
Sam F.
The price is AU$540
includes taxes & fees
21 Jan - 22 Jan
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
10.0 out of 10, Exceptional, (16 reviews)
"Our Hosts were wonderful and the space was great. It sits right off of the bike trail and across the street from a great bakery and bike shop. We thoroughly enjoyed our stay."
United States
Mark B.
The price is AU$276
includes taxes & fees
16 Jan - 17 Jan
Loft Apt Just off C&O near Harpers Ferry and AT
9.4 out of 10, Exceptional, (12 reviews)
"Great spot close to the wedding venue!!"
United States
Alfred T.
The price is AU$343
includes taxes & fees
13 Feb - 14 Feb
Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.
10.0 out of 10, Exceptional, (23 reviews)
"My friends and I absolutely loved this stay on the lake in West Virginia! The artsy vibe of the home, views, and wildlife were amazing. Plenty of places to sit and catch up. The kitchen was well stocked with appliances (thank you for the local coffee!) Each adult having their own bedroom and full bath was a huge perk!"
United States
Matthew P.
The price is AU$638
includes taxes & fees
15 Jan - 16 Jan
Art Docko - Lakefront Artist Retreat w/ Hot Tub!

Holiday Home in Downtown Frederick

*Luxury Condo In Downtown Frederick*
9.0 out of 10, Wonderful, (72 reviews)
"Very nice inside, clean, everything worked, chairs and beds were comfortable. Very nice stay.The backyard where we parked is a bit rough looking, and we're glad it didn't rain as walking from the car to the house is over rather thin grass/dirt. I pulled the car around to the front the night we got dressed up and went out. "
United States
Ray S.
The price is AU$390
includes taxes & fees
14 Jan - 15 Jan
*Luxury Condo In Downtown Frederick*
9.6 out of 10, Exceptional, (10 reviews)
"It was a great place to starve whole experience was perfect. "
United States
Jaime B.
The price is AU$576
includes taxes & fees
26 Jan - 27 Jan
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
9.2 out of 10, Wonderful, (30 reviews)
"Gorgeous cabin, incredibly clean and well stocked with everything needed. Hot tub was amazing and clean and huge. Greatful for the hosts promptness in communication.Thank you!"
United States
Samantha S.
The price is AU$419
includes taxes & fees
14 Jan - 15 Jan
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
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 favourite 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 depend 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 AU$159 per night. Entering your travel dates in the search wizard might find you 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.