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 NZ$318
includes taxes & fees
2 Mar - 3 Mar
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
10.0 out of 10, Exceptional, (142 reviews)
"Love the place will book again"
United States
WAYNE M.
The price is NZ$518
includes taxes & fees
22 Mar - 23 Mar
Charming "Cream of the Crop" Cape ~❤️of Middletown
9.8 out of 10, Exceptional, (71 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$175
includes taxes & fees
9 Mar - 10 Mar
❤️ 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$306
includes taxes & fees
2 Mar - 3 Mar
Pet-friendly, heart of downtown
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful location. Just what we were looking for."
United States
tony l.
The price is NZ$254
includes taxes & fees
1 Mar - 2 Mar
Birch Cabin at Hunting Creek Hideaway
9.8 out of 10, Exceptional, (67 reviews)
"Great stay! We would book again. "
United States
Sam F.
The price is NZ$612
includes taxes & fees
12 Mar - 13 Mar
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
10.0 out of 10, Exceptional, (64 reviews)
"We had a great time. House was very comfortable and location was perfect."
United States
Liz R.
The price is NZ$429
includes taxes & fees
1 Mar - 2 Mar
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
10.0 out of 10, Exceptional, (9 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.
The price is NZ$269
includes taxes & fees
27 Feb - 28 Feb
Bring Your Own Boat - Meticulously restored house on the Potomac River
10.0 out of 10, Exceptional, (6 reviews)
"Amazing stay love this place very cozy house ."
United States
Aimee C.
The price is NZ$351
includes taxes & fees
1 Mar - 2 Mar
Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown

Apartment in Frederick

Cozy, dog-friendly, downtown
10.0 out of 10, Exceptional, (28 reviews)
"Clean, great location, friendly owner"
United States
Christian M.
The price is NZ$317
includes taxes & fees
2 Mar - 3 Mar
Cozy, dog-friendly, downtown
9.2 out of 10, Wonderful, (89 reviews)
"This was an amazing cabin with a full kitchen so you could cook and enjoy the quiet."
United States
Lina A.
The price is NZ$537
includes taxes & fees
1 Mar - 2 Mar
Antietam Creek - Quiet 2 Bedroom Cabin
9.8 out of 10, Exceptional, (34 reviews)
"The cabin was very easy to get to, and yet it felt like you were in the middle of nowhere. The view was excellent. The accommodations were top-notch. I recommend this place to anyone."
United States
Greg R.
The price is NZ$583
includes taxes & fees
5 Mar - 6 Mar
Antietam Look Out - Incredible Sunset Views!
9.8 out of 10, Exceptional, (95 reviews)
"Love it been coming here for a few years now "
United States
Kristina M.
The price is NZ$429
includes taxes & fees
1 Mar - 2 Mar
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.

Holiday Home in Downtown Frederick

*Luxury Condo In Downtown Frederick*
9.0 out of 10, Wonderful, (77 reviews)
"Lovely place. It was perfect for our girls' trip long weekend. The rooms were so spacious and tastefully decorated. It was also super clean and had everything we needed, including for our night staying in with Door-dash to binge watch a couple Netflix series. The coffee lover in our group was so appreciative of the supplies and setup. The location is fabulous for walking the Creek Park, or to dinning and shopping options. We're looking forward to making this our Christmas present to each other...
United States
Lynne
The price is NZ$431
includes taxes & fees
1 Mar - 2 Mar
*Luxury Condo In Downtown Frederick*
9.2 out of 10, Wonderful, (31 reviews)
"Enjoyed the levels, hot tub, porch to get outside with my coffee, pet strolling area marvelous and washer/dryer."
United States
tracey b.
The price is NZ$462
includes taxes & fees
3 Mar - 4 Mar
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
3.0 star property
The price is NZ$719
includes taxes & fees
27 Feb - 28 Feb
Rural & Historic Detour Escape w/ Horses On-site!
10.0 out of 10, Exceptional, (1 review)
"We had a great time at Riverview Retreat! The house was perfect for our group and offered beautiful views. We especially loved the fireplace and all of the amenities they had available. The hot tub code was missing from the manual so we weren't able to use it on our first night and the spiral staircase was pretty intimidating for the weather we had. Heed the warnings about needing four wheel drive in the winter for the driveway. I was thankful there wasn't snow as it would have been scary to...
United States
Stacy H.
The price is NZ$687
includes taxes & fees
1 Mar - 2 Mar
Riverview Retreat - Pool, Hot Tub, and Mtn Views!
10.0 out of 10, Exceptional, (33 reviews)
"Lovely property, really nicely furnished and clean. Brilliant location for lots of places locally and close enough to walk into Leesburg itself to get ice cream!"
United Kingdom
Rachael B.
Leesburg Hideaway- King Bed + Private Backyard
9.6 out of 10, Exceptional, (21 reviews)
"Great place for a family weekend retreat. "
United States
Dina S.
The price is NZ$637
includes taxes & fees
1 Mar - 2 Mar
Peregrine's Perch - Cabin Overlooking the River!
10.0 out of 10, Exceptional, (5 reviews)
"Very clean, great amenities, comfortable!"
United States
James
The price is NZ$818
includes taxes & fees
2 Mar - 3 Mar
Private A-Frame Near Harpers Ferry - Sauna, Fire Pit, 3BR/3BA, Pet-Friendly
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$175 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?

Walk to Harpers Ferry! Dog-friendly. Beautiful Views.: This holiday home rental outside of Middletown offers a patio, a selection of games and a BBQ 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 that you can cook with friends or family.

How many holiday rentals will I find in Middletown?

Expedia has 6 holiday 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 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.