Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Middletown vacation rentals

Marina

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (21 reviews)
"Cleaned, beautifully decorated, not like a rental but more like a home!"
United States
Manjetjola P.
$265 nightly
The price is $281
Jun 10 - Jun 11
Total with taxes and fees
Historic Chesapeake City Stay
House (3 Bedrooms) | Interior

3 Mi to Dover Motor Speedway: Pet-friendly Retreat

3 Mi to Dover Motor Speedway: Pet-friendly Retreat
3.0 star property
Dover
$426 nightly
The price is $426
Jun 14 - Jun 15
Total with taxes and fees
3 Mi to Dover Motor Speedway: Pet-friendly Retreat
Property grounds

New Construction townhome close to everything downtown w/transparent pricing

New Construction townhome close to everything downtown w/transparent pricing
Hilltop
9.8 out of 10, Exceptional, (28 reviews)
"This condo was in a great location and was very clean and nice. Easy access to the beach and local restaurants and shops. "
United States
Peter F.
$179 nightly
The price is $184
Jun 8 - Jun 9
Total with taxes and fees
New Construction townhome close to everything downtown w/transparent pricing
Exterior

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
9.6 out of 10, Exceptional, (24 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
Jun 8 - Jun 9
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
1 bedroom

Summer Rustic Camping with AC and King Bed

Summer Rustic Camping with AC and King Bed
Elkton
9.8 out of 10, Exceptional, (6 reviews)
"This was a unique experience in a good way, very cool to sleep in the dome with windows to the sky and trees! Nice to know host is pet-friendly, even had paw towels and a water dish. We will bring our dog next time. The pellet stove made the rainy night and morning cozy."
United States
Deb F.
$156 nightly
The price is $157
Jun 9 - Jun 10
Total with taxes and fees
Summer Rustic Camping with AC and King Bed
Smart TV

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

Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (43 reviews)
"Wonderful place and host, very peaceful and quiet with plenty of nature !!!"
United States
Daniel V.
$105 nightly
The price is $111
Jun 15 - Jun 16
Total with taxes and fees
Country Get Away Studio Apartment
Outdoor dining

Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm
Nottingham
10.0 out of 10, Exceptional, (2 reviews)
"Property was close enough to stores and restaurants if needed. House is located in the rural area of the county (very peaceful). Property had all of the necessary kitchen utensil, pots, pans, and dishes that was needed for this trip. "
United States
jckglss6 G.
$185 nightly
The price is $186
Jun 8 - Jun 9
Total with taxes and fees
Amish Countryside Escape at Forest Edge Farm
Interior

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
10.0 out of 10, Exceptional, (2 reviews)
"Nice clean place. Highly recommended."
United States
Richard B.
$148 nightly
The price is $152
Jun 23 - Jun 24
Total with taxes and fees
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
1 bedroom, desk, WiFi, bed sheets

White Clay Creek Cottage

White Clay Creek Cottage
Newark
10.0 out of 10, Exceptional, (7 reviews)
"We needed a somewhat local place to stay while my house was sold before moving into the new house a few days later. This was the perfect spot for us. the home was nicely equipped for us and allowed our small dog to visit too. "
United States
tracy g.
$197 nightly
The price is $197
Jun 10 - Jun 11
Total with taxes and fees
White Clay Creek Cottage
Shower, hair dryer, towels, soap

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

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Havre de Grace
10.0 out of 10, Exceptional, (10 reviews)
"The house was very cozy and close to my venue Jennifer was very responsive with any questions nice place to stay roomy"
United States
Liza
$243 nightly
The price is $257
Jun 9 - Jun 10
Total with taxes and fees
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Terrace/patio

Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
10.0 out of 10, Exceptional, (1 review)
"This unit is located behind a mansion /b&b. Had what we needed, clean, easy to access and Karin was helpful."
United States
Megan M.
$230 nightly
The price is $239
Jun 7 - Jun 8
Total with taxes and fees
Tiny Home Tranquil Oasis
Dining

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, (22 reviews)
"Very nice property, just right size for our needs. Great neighborhood. Kitchen very nice, check in easy."
United States
Lori W.
$325 nightly
The price is $333
Jun 9 - Jun 10
Total with taxes and fees
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Terrace/patio

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
$219 nightly
The price is $228
Jun 7 - Jun 8
Total with taxes and fees
Nature's Haven Tiny Home
TV, computer monitors

3 Mi to Dover Motor Speedway: Pet-Friendly Retreat

3 Mi to Dover Motor Speedway: Pet-Friendly Retreat
Dover
9.0 out of 10, Wonderful, (7 reviews)
"Great property in a quiet neighborhood. Owner communicated easily and effectively. "
United States
Patrick C.
$436 nightly
The price is $440
Jun 14 - Jun 15
Total with taxes and fees
3 Mi to Dover Motor Speedway: Pet-Friendly Retreat
Fridge, microwave, oven, stovetop

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
10.0 out of 10, Exceptional, (3 reviews)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
$324 nightly
The price is $343
Jun 16 - Jun 17
Total with taxes and fees
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Exterior

Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (20 reviews)
"Everything was good. Had a great time."
United States
Todd H.
$450 nightly
The price is $497
Jun 17 - Jun 18
Total with taxes and fees
Thunder Hill Retreat - Spacious/Deck/Hot tub
Fridge, microwave, oven, stovetop

Quarry Landing - Center of Town & River View - 3 Bedroom

Quarry Landing - Center of Town & River View - 3 Bedroom
Port Deposit
10.0 out of 10, Exceptional, (12 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
$277 nightly
The price is $293
Jun 9 - Jun 10
Total with taxes and fees
Quarry Landing - Center of Town & River View - 3 Bedroom
Fridge, microwave, oven, stovetop

Two-story condo in luxury townhouse. Free parking.

Two-story condo in luxury townhouse. Free parking.
Downtown Wilmington
9.6 out of 10, Exceptional, (18 reviews)
"Comfortable place, wonderful amenities, and a gracious host. "
United States
Donald H.
$349 nightly
The price is $359
Jun 7 - Jun 8
Total with taxes and fees
Two-story condo in luxury townhouse. Free parking.
Beach

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

Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
Newark
$161 nightly
The price is $177
Jun 7 - Jun 8
Total with taxes and fees
Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
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

Ramada by Wyndham Newark/Wilmington

Ramada by Wyndham Newark/Wilmington

2/10 Terrible
"Helpful front desk staff, but the hotel did not reach a baseline of cleanliness and safety I needed for my stay."
Chris 2-night trip
Posted 2 hours ago
Ramada by Wyndham Newark/Wilmington

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. 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.