Holiday Rentals Middletown from £87: Find Short-Term Rentals & Holiday Accommodations

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.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Middletown holiday rentals

A bunk bed room with white bedding and blue throw blankets.

1. Bohemia Manor Farm

Chesapeake City

includes taxes & fees

13 Oct - 14 Oct

A riverside dock with boats, a covered seating area, and a bridge in the background.

2. Historic Chesapeake City Stay

Chesapeake City

Martha J.

includes taxes & fees

28 Sept - 29 Sept

A covered deck area with a grill and outdoor seating.

3. Nature's Haven Tiny Home

Bear

Maxwell

includes taxes & fees

28 Sept - 29 Sept

4. Tiny Home Tranquil Oasis

Bear

Erin C.

includes taxes & fees

28 Sept - 29 Sept

A boat interior with a white leather sofa, a cushioned bench, a television, and a view of the outside.

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

Bear

"My boyfriend and I had a fantastic night on the yacht. We arrived right on time and found the AC and the lights on and ready for our arrival. I sunbathed on the front of the yacht and danced on the back after dinner at Grain H2O. The restaurant is located at the top of the hill on the marina . There was a band and we could hear the music from the boat. The marina was clean and everyone is friendly. At night it was very peaceful and easy to fall asleep. The morning we enjoyed our last couple of...

Karen

includes taxes & fees

29 Sept - 30 Sept

A two-story residential building with a stone facade, a large front lawn, and a driveway.

6. Elegant Family Stay • Quiet Neighborhood • Comfort

New Castle

Daniel J.

includes taxes & fees

1 Oct - 2 Oct

A wooden cabin with a porch, surrounded by dense forest.

7. Country Get Away Studio Apartment

Elkton

JAMES V.

includes taxes & fees

7 Oct - 8 Oct

A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

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

Millington

Riley B.

includes taxes & fees

28 Sept - 29 Sept

View all properties

Find holiday rentals that suit your style

Apartments

Houseboats

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Middletown Hotel Reviews

Hampton Inn Middletown

10/10 Excellent

"Excellent customer service We service"

SureStay Plus Hotel by Best Western Brandywine Valley

10/10 Excellent

"We were in town for the HORROR FEST FILM FESTIVAL. Check-in was super easy and the staff was delightful. Our room was very clean, well prepped, and slept well. The only dislike was the loud neighbor, but I will not hold that against the place. The breakfast was great and filling, lots of options. Definitely recommend for anyone traveling though. Great shampoo provided. Good prices, and an actual modern tv that was nice to relax watching during the 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 £87 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 5 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 The Everett Annex and Everett Theatre, 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.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates