Photo by Michelle Gonzalez

Middletown Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Sep 24 - Sep 25
Tomorrow
Sep 25 - Sep 26
This weekend
Sep 26 - Sep 28
Next weekend
Oct 3 - Oct 5

Vacation Rentals in Middletown

Our top choices for Middletown vacation rentals

Luxurious and spacious townhome with all necessary amenities awaits your stay.
Fridge, microwave, oven, stovetop

Luxurious and spacious townhome with all necessary amenities awaits your stay.

9.4 out of 10, Exceptional, (9)
"Great experience all around! "
Luxurious and spacious townhome with all necessary amenities awaits your stay.
Tip Of The Town Fresh and New 3 Bedroom Nest
Fridge, microwave, oven, stovetop

Tip Of The Town Fresh and New 3 Bedroom Nest

10.0 out of 10, Exceptional, (25)
"Was a great clean place located in a nice little town! Would definitely recommend it!"
Tip Of The Town Fresh and New 3 Bedroom Nest
Charming 2-bedroom cabin close to Fair Hill on horse farm
Interior

Charming 2-bedroom cabin close to Fair Hill on horse farm

9.4 out of 10, Exceptional, (6)
"Good experience"
Charming 2-bedroom cabin close to Fair Hill on horse farm
Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.
Fridge, microwave, oven, stovetop

Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.

8.4 out of 10, Very Good, (8)
"Was in Wilmington to work a trade show at the Chase Center on the Riverfront. Everything was as described and the communications with the host were great. Only about a 12 minute drive to the venue and lots of restaurants within a 10 minute drive. It’s nothing fancy but for about the same price as a budget hotel room you get a kitchen, two comfy bedrooms and a living room. "
The price is ￥16,237
￥27,596 total
includes taxes & fees
Sep 26 - Sep 27
Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Fridge, microwave, oven, stovetop

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (40)
"The house was perfect for 6 young adults! We were only 5 minutes from Anchor Marina which was perfect for our group. The fire pit and outdoor set up was nice and we had plenty of space for everyone. "
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Interior

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

9.8 out of 10, Exceptional, (19)
"Clean and comfortable stay in quiet neighborhood! Communication with the host was pleasant and prompt."
The price is ￥28,582
￥49,219 total
includes taxes & fees
Sep 25 - Sep 26
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Chesapeake Bay House with Dock & Private Beach
Outdoor dining

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (172)
"Property was in good shape and had plenty of space. Our family loved the beach and the shallow water for the children to play in. Even though we didn’t have perfect weather, we had a wonderful trip."
Chesapeake Bay House with Dock & Private Beach
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Smart TV, books

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (57)
"Lovely cottage, well-equipped, immaculately clean. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
Interior

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

9.2 out of 10, Wonderful, (179)
"Perfect spot for a relaxing weekend on the water, even if the kids are playing in a sports tournament."
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
Waterfront house with amazing views. Top of the Chesapeake
Terrace/patio

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (100)
"The water views, sunrises, and many local birds, including a nearby osprey nest, were all spectacular. The whole back of the house is a bank of windows (living room and master bedroom). It feels private as your view is just your outdoor lounge area, dock, and the water. No big downsides (minorly need space for tooth brushes as the sinks are mostly the sink bowls). Everything was clean,and comfortable. In similar off the beaten path vrbo's we've had lower cleanliness or ants, but not here! ...
Waterfront house with amazing views. Top of the Chesapeake
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Iron/ironing board, WiFi, bed sheets

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

2.0 star property
9.6 out of 10, Exceptional, (5)
"Great stay. Everything you need, quiet and clean. "
The price is ￥17,713
￥23,783 total
includes taxes & fees
Sep 30 - Oct 1
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Historic Chesapeake City Stay
Marina

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (15)
"Always a nice get away…."
The price is ￥15,942
￥40,525 total
includes taxes & fees
Oct 2 - Oct 3
Historic Chesapeake City Stay
Charming 2-bedroom house with WiFi, AC in marvelous Wilmington
Fridge, microwave, oven, stovetop

Charming 2-bedroom house with WiFi, AC in marvelous Wilmington

2.0 out of 10, (1)
"Never heard from host. Expedia had to cancel reservation."
The price is ￥14,761
￥18,377 total
includes taxes & fees
Oct 5 - Oct 6
Charming 2-bedroom house with WiFi, AC in marvelous Wilmington
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Fridge, microwave, oven, stovetop

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

9.8 out of 10, Exceptional, (47)
"This property was perfect for our trip. It was very clean, comfortable and feels like home. Description and photos on the website were accurate. The owners were very attentive and hospitable. This is definite a place I’ll return to."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!
Terrace/patio

Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!

10.0 out of 10, Exceptional, (2)
"The house is amazing. Very clean and accessible. Carrie and Mike were amazing host . The backyard is truly an oasis. "
Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!
Nancy’s Touch, A Waterfront Paradise!
Terrace/patio

Nancy’s Touch, A Waterfront Paradise!

10.0 out of 10, Exceptional, (169)
"Absolutely fantastic place to stay. When we walked in, it just felt so comfortable. The gardens are beautiful and we were able to see Eagles most every day. Communication was excellent. "
Nancy’s Touch, A Waterfront Paradise!
Tiny Home Tranquil Oasis
Fridge, microwave, oven, stovetop

Tiny Home Tranquil Oasis

The price is ￥27,898
￥35,649 total
includes taxes & fees
Sep 26 - Sep 27
Tiny Home Tranquil Oasis
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Beach nearby, sun loungers, beach towels

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

9.6 out of 10, Exceptional, (44)
"This is a jewel as it is private, peaceful with lovely setting."
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Quarry Landing - Center of Town & River View - 3 Bedroom
Property grounds

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

9.8 out of 10, Exceptional, (9)
"Great stay in a relaxing community. We loved to be able to walk to places from the house! The hosts were very helpful and easy to communicate with 💙"
The price is ￥24,461
￥37,202 total
includes taxes & fees
Sep 25 - Sep 26
Quarry Landing - Center of Town & River View - 3 Bedroom
5-bedroom vacation home 5 minutes from historic Charlestown
Sun loungers, beach towels

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (144)
"Nice property with amazing views. Celebrated college graduation with family. Young ones had fun looking at ducks. Plenty of room for a large group."
The price is ￥43,973
￥84,006 total
includes taxes & fees
Sep 30 - Oct 1
5-bedroom vacation home 5 minutes from historic Charlestown
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.
View all properties
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

DoubleTree by Hilton Downtown Wilmington - Legal District

DoubleTree by Hilton Downtown Wilmington - Legal District

10/10 Excellent
"The Quiet The bathroom could be cleaned a little bit better "
Mario 4-night trip
Posted 13 hours ago
DoubleTree by Hilton Downtown Wilmington - Legal District

Find out more about Middletown

Find out more about Middletown

Search for holiday rentals in Middletown on Expedia! You can easily find your home rentals, villas, holiday apartments in Middletown using one of the methods below:

  • View our selection of featured holiday rentals in Middletown
  • Use the map to find apartments and other holiday homes in the Middletown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Middletown while they last

Look no further and take a look at our great range of rental properties in Middletown!

Explore a world of travel with Expedia

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?

Tip Of The Town Fresh and New 3 Bedroom Nest: This vacation home rental near Middletown offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Middletown?

With 5 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, Back Creek Golf Club 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.