A steel arch bridge over a river with surrounding trees and buildings.

Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Middletown vacation rentals

Marina

1. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (25 reviews)
"The rental was perfect for what we needed. The bed and living room furniture were very comfortable and the kitchen well stocked. The host was quick to respond to questions I had. I will definitely see if this rental if available the next time I’m in the area."
United States
Martha J.
$265 nightly
The price is $281
Aug 9 - Aug 10
Total with taxes and fees
Historic Chesapeake City Stay
Exterior

2. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (45 reviews)
"Perfect in every way… a great stay"
United States
Robert B.
$105 nightly
The price is $111
Aug 10 - Aug 11
Total with taxes and fees
Country Get Away Studio Apartment
Exterior

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

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.8 out of 10, Exceptional, (23 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
$118 nightly
The price is $125
Aug 10 - Aug 11
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
Terrace/patio

4. Nature's Haven Tiny Home

Nature's Haven Tiny Home
Bear
10.0 out of 10, Exceptional, (4 reviews)
"Great place to relax after a while on the go. Karin was very friendly and informative about places to see in the area. Everything was great "
United States
Maxwell
$225 nightly
The price is $234
Aug 3 - Aug 4
Total with taxes and fees
Nature's Haven Tiny Home
Terrace/patio

5. Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
10.0 out of 10, Exceptional, (2 reviews)
"This was a stop over on our way to the beach- it was a convenient comfy space for our family."
United States
Erin C.
$232 nightly
The price is $241
Aug 2 - Aug 3
Total with taxes and fees
Tiny Home Tranquil Oasis
Interior

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

Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
Bear
10.0 out of 10, Exceptional, (1 review)
"The hosts are wonderful! Easy to communicate with and they answer all questions so quickly. We absolutely loved our stay on this beautiful boat and would absolutely do it again. Highlight of our summer vacation."
United States
Bonnye B.
$286 nightly
The price is $297
Aug 4 - Aug 5
Total with taxes and fees
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
Coffee/tea maker, fridge, microwave, oven

7. Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Elkton
9.6 out of 10, Exceptional, (5 reviews)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
$331 nightly
The price is $351
Aug 17 - Aug 18
Total with taxes and fees
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Exterior

8. Elegant Family Stay • Quiet Neighborhood • Comfort

Elegant Family Stay • Quiet Neighborhood • Comfort
New Castle
10.0 out of 10, Exceptional, (10 reviews)
"Place was very clean and the host was EXCELLENT with fast communication "
United States
Chris R.
$384 nightly
The price is $397
Aug 6 - Aug 7
Total with taxes and fees
Elegant Family Stay • Quiet Neighborhood • Comfort
House (3 Bedrooms) | Interior

9. Dover Home Base: 3 Mi to Motor Speedway!

Dover Home Base: 3 Mi to Motor Speedway!
3.0 star property
Dover
Dover Home Base: 3 Mi to Motor Speedway!
Dining

10. Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Newark
9.6 out of 10, Exceptional, (24 reviews)
"Very nice property, just right size for our needs. Great neighborhood. Kitchen very nice, check in easy."
United States
Lori W.
$349 nightly
The price is $359
Aug 19 - Aug 20
Total with taxes and fees
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Interior

11. Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
Dover
9.8 out of 10, Exceptional, (9 reviews)
"Woodland Hideaway was just that! A nice place to hideaway after hot and busy days. The place was clean, kitchen well stocked and the whole unit was quiet. It was located in a nice subdivision with lots of trees and beautiful flowers. It was the first trip my husband and I took our dog and it was a great place for the dog, quiet with lots of places for his daily walks. Thank you Kara!"
United States
Melanie
$170 nightly
The price is $175
Aug 13 - Aug 14
Total with taxes and fees
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
Exterior

12. Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Elkton
10.0 out of 10, Exceptional, (12 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
$152 nightly
The price is $161
Aug 8 - Aug 9
Total with taxes and fees
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Property grounds

13. Sunset River Shack -amazing waterfront view

Sunset River Shack -amazing waterfront view
Elkton
9.6 out of 10, Exceptional, (7 reviews)
"The home is nice The view from the deck was wonderful But there wasn’t access to the water Easy to find and we really enjoyed the area"
United States
Hope D.
$421 nightly
The price is $446
Aug 3 - Aug 4
Total with taxes and fees
Sunset River Shack -amazing waterfront view
Terrace/patio

14. Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
Newark
9.8 out of 10, Exceptional, (6 reviews)
"Enjoyed our stay."
United States
Erik H.
$371 nightly
The price is $371
Sep 1 - Sep 2
Total with taxes and fees
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
Interior

15. Charming 3-bedroom house in wonderful Pennsville Township with AC, WiFi

Charming 3-bedroom house in wonderful Pennsville Township with AC, WiFi
Pennsville Township
$285 nightly
The price is $314
Aug 2 - Aug 3
Total with taxes and fees
Charming 3-bedroom house in wonderful Pennsville Township with AC, WiFi
Property grounds

16. New Construction townhome close to everything downtown w/transparent pricing

New Construction townhome close to everything downtown w/transparent pricing
Hilltop
9.6 out of 10, Exceptional, (29 reviews)
"There were 3 of us ladies for the week. Lisa was a great host and recommendations were all perfect. We will definitely be back. Everything was clean and neat. We loved staying there. "
United States
Bonnie W.
$184 nightly
The price is $189
Aug 11 - Aug 12
Total with taxes and fees
New Construction townhome close to everything downtown w/transparent pricing
Beach

17. Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!

Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
Newark
$185 nightly
The price is $203
Aug 9 - Aug 10
Total with taxes and fees
Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
Property grounds

18. Beachcomber Suite

Beachcomber Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...
United States
Lisa E.
$167 nightly
The price is $181
Aug 10 - Aug 11
Total with taxes and fees
Beachcomber Suite
TV, books, stereo

19. Cozy House in a Quiet Neighborhood

Cozy House in a Quiet Neighborhood
Wilmington
$180 nightly
The price is $186
Aug 9 - Aug 10
Total with taxes and fees
Cozy House in a Quiet Neighborhood
Property grounds

20. Entire place with private parking

Entire place with private parking
Hilltop
8.0 out of 10, Very Good, (11 reviews)
"great place very clean. Will stay again loved private parking "
United States
kennya J.
$151 nightly
The price is $155
Aug 3 - Aug 4
Total with taxes and fees
Entire place with private parking
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

Best Western Plus Newark/Christiana Inn

Best Western Plus Newark/Christiana Inn

8/10 Good
"The room was clean. Breakfast was good."
Brenda 1-night trip
Posted 1 hour ago
Best Western Plus Newark/Christiana Inn

Find out more about Middletown

Everything you need to know about Middletown vacation rentals

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

Middletown vacation 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 low season months. For more hustle and bustle, you may prefer to visit Middletown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $351 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Middletown?

Yes, you can find vacation rentals in Middletown close to Frightland, or you can choose a secluded option if you're looking for extra privacy while you relax. Our travelers 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 vacation rentals that Middletown has to offer?

Sunset River Cottage: This vacation home rental near Middletown is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Middletown?

With 8 Expedia vacation rentals, you're sure 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 vacation rentals like in Middletown?

Vacation rentals are private accommodations you can stay in for several days or more in Middletown. Vacation rentals provide amenities such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for family gatherings.