Middletown Holiday Rentals from €252: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Middletown has to offer?

Sailor's Sunrise Cottage - Chesapeake Bay : This holiday home rental outside of Middletown is located on a lake, and has a fireplace, a garden and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

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Our top choices for Middletown holiday rentals

Spacious Middletown Family Retreat - Sleeps 8

Middletown

includes taxes & fees

13 Jul - 14 Jul

Nature's Haven Tiny Home

Bear

Maxwell

includes taxes & fees

8 Jul - 9 Jul

Tiny Home Tranquil Oasis

Bear

Megan M.

includes taxes & fees

21 Jul - 22 Jul

Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail

Bear

includes taxes & fees

9 Jul - 10 Jul

Historic Chesapeake City Stay

Chesapeake City

Manjetjola P.

includes taxes & fees

13 Jul - 14 Jul

Country Get Away Studio Apartment

Elkton

Robert B.

includes taxes & fees

14 Jul - 15 Jul

Guest Suite for up to 2 in a Victorian on the Chester River

Millington

Riley B.

includes taxes & fees

8 Jul - 9 Jul

Summer Rustic Camping with AC and King Bed

Elkton

Rees L.

includes taxes & fees

8 Jul - 9 Jul

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Top Middletown Hotel Reviews

Staybridge Suites Wilmington Downtown by IHG

10/10 Excellent

"Me and my 2 boys were able to stay comfortably in the 2 bed with 1 pullout suite. There was a kitchenette with all kitchen items needed, which was awesome. The staff was very friendly, always saying hello and have a good day. When we 1st got there I was hicked about the parking price but there was always available street parking. If you worked it right, you may not have to pay much. The only thing I would recommend is to have a normal size trash can in the rooms where you can cook instead if the bathroom sized cans. I was told there should have been an extra big one under the sink, but it was another small one. Overall this was a great stay!"

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, apart-hotels, 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 €252 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 in Middletown close to Frightland, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Middletown has a good selection of restaurants. Make sure you have time to check out the festivals and churches during your trip.

What are some of the best holiday rentals that Middletown has to offer?

Sailor's Sunrise Cottage - Chesapeake Bay: This holiday home rental outside of Middletown is located on a lake, and has a fireplace, a garden and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

How many holiday rentals are there in Middletown?

With 7 Expedia holiday rentals, you're guaranteed to find just the right place for your Middletown stay.

What can I see and do in Middletown?

Cultural attractions include Everett Theatre and The Everett Annex, whereas Frightland is just one of the family-friendly sights. While here, Middletown Historic District and Middletown Town Hall are other places worth a visit.

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 feature extras such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy lobbies while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for family trips.

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Our top choices for Middletown holiday rentals