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. Make the most of the hot tub in this rental home to help you unwind.

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Our top choices for Middletown vacation rentals

Country Get Away Studio Apartment

Elkton

Daniel V.

$105 nightly

Jun 10 - Jun 11

Total with taxes and fees

Historic Chesapeake City Stay

Chesapeake City

Manjetjola P.

$265 nightly

Jun 10 - Jun 11

Total with taxes and fees

Summer Rustic Camping with AC and King Bed

Elkton

Rees L.

$165 nightly

Jun 10 - Jun 11

Total with taxes and fees

3 Mi to Dover Motor Speedway: Pet-friendly Retreat

Dover

$427 nightly

Jun 14 - Jun 15

Total with taxes and fees

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

Elkton

Melissa J.

$152 nightly

Jun 4 - Jun 5

Total with taxes and fees

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

Millington

Riley B.

$118 nightly

Jun 8 - Jun 9

Total with taxes and fees

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

Dover

Richard B.

$141 nightly

Jun 10 - Jun 11

Total with taxes and fees

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

Havre de Grace

Liza

$202 nightly

Jun 9 - Jun 10

Total with taxes and fees

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Top Middletown Hotel Reviews

Embassy Suites by Hilton Newark Wilmington South

10/10 Excellent

"This was my second stay at this fantastic hotel in the last 30 days. They did not disappoint. The staff are absolutely fantastic. Sylvia was very caring and professional and took great care of us again on this trip. Malcolm checked us in very easy, quickly. The serving staff, Irma, Sandra, Jouana and Anastasia, and the 2 chefs were just as caring as before and great. Overall, this hotel is a great value, great amenities, clean, good size rooms, delicious breakfast, but again, most important of all, the team members are fantastic. I thank Sylvia and all other team members for their dedication and great customer care. I, fully intend to be back in a few days again."

Best Western Plus Newark/Christiana Inn

6/10 Okay

"The carpet and the drapes were in need of being cleaned or replaced.The coffee machine was out of order and the alternatives provided did not offer decaf or hot water for tea.The front desk staff was kind, courteous, very pleasant and extremely helpful. The air conditioning in the room was able to be adjusted to a comfortable level but in the area where breakfast was served it was cold and uncomfortable.The swimming pool was extremely cold and the hot tub was out of serve.Towels were not readily available in the pool area they had to be requested at the front desk.Overall I felt the accommodations were less than adequate for the price and I would not recommend it if other accommodations are available."

Staybridge Suites Wilmington Downtown by IHG

2/10 Terrible

"During our stay at this hotel, cash was stolen from our room while we were at breakfast. We always make sure to close and secure the door, so this was extremely alarming. When we reported the incident, the manager suggested that we must not have closed the door properly, which felt dismissive and unhelpful. They also implied that “not enough time had passed” for a theft to occur — an assumption that did nothing to address the seriousness of the situation. We asked for the key‑log records for our room, but instead of showing them to us, staff simply stated that only guest passes were used. Without transparency, it was impossible to feel reassured or confident in their explanation. Police report was filed. Overall, the lack of accountability and the way the situation was handled left us very disappointed. Security and honesty should be a priority for any hotel, and unfortunately, that was not our experience here."

Sonesta Select Newark Christiana Mall

6/10 Okay

"Please vacuum more. The guest were very hard on this property while were with you. The amount of trash in the halls made our visit a bad one. Our toilet was draining slow we used the lobby one frequently. The location was good for our needs. We will choose another hotel closer to our destination on our next visit."

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.

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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. Make the most of the hot tub in this rental home to help you unwind.

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 Town Hall and Frog Hollow Golf Club 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.

Middletown Vacation Rentals

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Our top choices for Middletown vacation rentals

Country Get Away Studio Apartment

Historic Chesapeake City Stay

Summer Rustic Camping with AC and King Bed

3 Mi to Dover Motor Speedway: Pet-friendly Retreat

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

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

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

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

Amish Countryside Escape at Forest Edge Farm

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

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

Thunder Hill Retreat - Spacious/Deck/Hot tub

New Construction townhome close to everything downtown w/transparent pricing

Nature's Haven Tiny Home

Tiny Home Tranquil Oasis

3 Mi to Dover Motor Speedway: Pet-Friendly Retreat

Two-story condo in luxury townhouse. Free parking.

Modern 1BR in Downtown Wilmington Near Riverwalk & Restaurants

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

Find vacation rentals that suit your style

Top Middletown Hotel Reviews

Embassy Suites by Hilton Newark Wilmington South

Find out more about Middletown

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