Middletown Vacation Rentals from $111: Search Short-Term Rentals

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

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

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Middletown vacation rentals

1. Historic Chesapeake City Stay

Chesapeake City

Martha J.

$253 nightly

Sep 23 - Sep 24

Total with taxes and fees

2. Country Get Away Studio Apartment

Elkton

JAMES V.

$105 nightly

Sep 28 - Sep 29

Total with taxes and fees

2 bedrooms, iron/ironing board, WiFi (free), bed sheets

3. HISTORIC WATERFRONT 2 Bedrooms/4 beds in Chesapeake City with AC

Chesapeake City

Deb D.

$281 nightly

Sep 21 - Sep 22

Total with taxes and fees

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

Millington

Riley B.

$118 nightly

Sep 21 - Sep 22

Total with taxes and fees

5. Nature's Haven Tiny Home

Bear

Maxwell

$225 nightly

Sep 20 - Sep 21

Total with taxes and fees

6. Tiny Home Tranquil Oasis

Bear

Erin C.

$233 nightly

Sep 20 - Sep 21

Total with taxes and fees

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

Bear

Justin M.

$286 nightly

Sep 22 - Sep 23

Total with taxes and fees

Luxury House, Multiple Bedrooms, Lake View | Laptop workspace, WiFi (free)

8. Bohemia Manor Farm

Chesapeake City

$392 nightly

Oct 20 - Oct 21

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Cabins

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

Bally's Dover Casino Resort

10/10 Excellent

"Staff was very friendly. Hotel was clean and nicely decorated. Dinner at Longo’s was excellent, and the casino was so much fun."

Best Western Plus Newark/Christiana Inn

8/10 Good

"Nice hotel. Beautiful pool and spa. We got in late so didn’t get to use the pool. Was awakened at 5 in the morning to equate as the hotel was flooded. A water main break! We waited outside for an hour. Everyone started to leave.’no one told us anything. We drove to our next destination in a pouring rainstorm."

DoubleTree by Hilton Hotel Wilmington

8/10 Good

"Upon check-in we were welcomed by Corey who was professional and courteous. There was an issue with the main corridor was extremely hot as if no ac was on. I came down to the front desk and a manager who I believe was Mr. Brown took care of it immediately. Upon checking out the woman at the front desk (don’t recall her name) was also very nice, professional and eager to assist. All staff was professional and courteous except the woman bartender who had more interest with her phone than she did with assisting customers. I waited and watched her and a man discuss something about her phone for over 15 mins while I waited to order a drink. When she finally did approach me, she was not friendly and showed no customer service. Room was fine, bed was comfortable, but attention to details in the bathroom are needed. Wallpaper peeling and nicks on the wall under the left side of the sink and can be seen while using the toilet. Due to hotel being so busy and noisy due to a catered event (wedding I think) and main door didn’t work. Overall hotel condition is 3, but all of the staff (except bartender) is a 5 which brought the rating up to a 4."

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 $111 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?

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

How many vacation rentals are there in Middletown?

With 6 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 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 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.

Room 1

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Middletown vacation rentals

1. Historic Chesapeake City Stay

2. Country Get Away Studio Apartment

3. HISTORIC WATERFRONT 2 Bedrooms/4 beds in Chesapeake City with AC

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

5. Nature's Haven Tiny Home

6. Tiny Home Tranquil Oasis

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

8. Bohemia Manor Farm

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

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

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

12. Elegant Family Stay • Quiet Neighborhood • Comfort

13. Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..

14. Cozy Comfy Pet Friendly House in a Quiet Neighborhood

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

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

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

18. Beachcomber Suite

19. Turtle Cove Room

Find vacation rentals that suit your style

Top Middletown Hotel Reviews

Bally's Dover Casino Resort

DoubleTree by Hilton Downtown Wilmington - Legal District

Sonesta Select Newark Christiana Mall

Best Western Plus Newark/Christiana Inn

Embassy Suites by Hilton Newark Wilmington South

DoubleTree by Hilton Hotel Wilmington

SureStay Plus Hotel by Best Western Brandywine Valley

Hampton Inn Middletown

Find out more about Middletown

Explore a world of travel with Expedia

Frequently asked questions

Expedia's Latest Trends

Go further with the Expedia app