Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Middletown vacation rentals

Interior

Heated Pool • Private Backyard • Home Theater

Heated Pool • Private Backyard • Home Theater
Middletown
The price is ￥8,804
￥71,717 total
includes taxes & fees
Feb 10 - Feb 11
Heated Pool • Private Backyard • Home Theater
Exterior

Country Get Away 1 Bedroom Apartment

Country Get Away 1 Bedroom Apartment
Elkton
9.8 out of 10, Exceptional, (40 reviews)
"The accommodation description is good; the actual accommodations are great, better than expected, truly a quiet country getaway with many unexpected extras. Deciding to stay here was great decision. It's done right."
United States
John L.
The price is ￥11,005
￥17,498 total
includes taxes & fees
Feb 16 - Feb 17
Country Get Away 1 Bedroom Apartment
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, (19 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is ￥10,691
￥19,665 total
includes taxes & fees
Feb 10 - Feb 11
Guest Suite for up to 2 in a Victorian on the Chester River
Terrace/patio

Amazing Modern house with a full kitchen and parking

Amazing Modern house with a full kitchen and parking
Smyrna
9.2 out of 10, Wonderful, (9 reviews)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
United States
Laurie S.
The price is ￥16,980
￥42,742 total
includes taxes & fees
Feb 10 - Feb 11
Amazing Modern house with a full kitchen and parking
Interior

JVA LUXURY HOUSING

JVA LUXURY HOUSING
Smyrna
10.0 out of 10, Exceptional, (1 review)
"The house was clean and wonderful. I highly recommend!"
United States
Daryl C.
The price is ￥62,888
￥92,603 total
includes taxes & fees
Feb 16 - Feb 17
JVA LUXURY HOUSING
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, (21 reviews)
"Very nice property, just right size for our needs. Great neighborhood. Kitchen very nice, check in easy."
United States
Lori W.
The price is ￥30,422
￥52,387 total
includes taxes & fees
Feb 11 - Feb 12
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Exterior

Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (19 reviews)
"Had a nice stay."
United States
Todd H.
The price is ￥27,238
￥70,186 total
includes taxes & fees
Feb 10 - Feb 11
Thunder Hill Retreat - Spacious/Deck/Hot tub
Fridge, microwave, oven, stovetop

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

Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.
Wilmington
8.8 out of 10, Excellent, (19 reviews)
"Very quiet place with comfortable bed. Great overnight stay!"
United States
Rhonda Y.
The price is ￥15,565
￥27,586 total
includes taxes & fees
Feb 15 - Feb 16
Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.
Smart TV, fireplace, video games, books

Water front home on the Cohansey River

Water front home on the Cohansey River
Bridgeton
10.0 out of 10, Exceptional, (25 reviews)
"The stay was fantastic, it is right on the river, fishing was good (caught some huge catfish), the pool was A+ for hot days, and we had an overall wonderful time. Kitchen was extremely well stocked, plenty of space for sleeping and hanging out, and a fire under the stars is a special treat we were able to enjoy."
United States
James R.
The price is ￥62,102
￥126,559 total
includes taxes & fees
Feb 16 - Feb 17
Water front home on the Cohansey River
TV, fireplace

Long Beach Cottage, (romantic couple’s getaway)

Long Beach Cottage, (romantic couple’s getaway)
Charlestown
10.0 out of 10, Exceptional, (5 reviews)
"Loved the property and the decor. Very well done and luxurious!"
United States
Elisheva K.
The price is ￥51,068
￥79,520 total
includes taxes & fees
Feb 17 - Feb 18
Long Beach Cottage, (romantic couple’s getaway)
Property grounds

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, (23 reviews)
"Property was spacious with open kitchen/living room area and 2 bedrooms with their own baths."
United States
Mark F.
The price is ￥18,866
￥27,733 total
includes taxes & fees
Feb 10 - Feb 11
New Construction townhome close to everything downtown w/transparent pricing
1 bedroom

Summer Rustic Camping with AC and King Bed

Summer Rustic Camping with AC and King Bed
Elkton
9.6 out of 10, Exceptional, (5 reviews)
"The owners were very attentive to our needs, and everything was exactly as advertised. We came up for a horse show in Maryland and the convenience to the grounds was exceptional, and everything was wonderful from the privacy to the beauty of the property."
United States
Rees L.
The price is ￥11,029
￥23,795 total
includes taxes & fees
Feb 10 - Feb 11
Summer Rustic Camping with AC and King Bed
TV, fireplace

The Gilpin Getaway | 2BR | Free Coffee | by RedAwning

The Gilpin Getaway | 2BR | Free Coffee | by RedAwning
Trolley Square
7.6 out of 10, Good, (4 reviews)
"This unit is very much as depicted in photos on VRBO site. The neighborhood is interesting and feels safe, and the unit itself is very authentic to residential multi units built, I'm guessing, about 100 years ago. We recommend this place. "
United States
Thomas D.
The price is ￥16,757
￥59,570 total
includes taxes & fees
Feb 10 - Feb 11
The Gilpin Getaway | 2BR | Free Coffee | by RedAwning
Property grounds

Entire place with private parking

Entire place with private parking
Hilltop
7.6 out of 10, Good, (10 reviews)
"great place very clean. Will stay again loved private parking "
United States
kennya J.
The price is ￥13,835
￥23,105 total
includes taxes & fees
Feb 10 - Feb 11
Entire place with private parking
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, (11 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is ￥20,942
￥33,364 total
includes taxes & fees
Feb 11 - Feb 12
Quarry Landing - Center of Town & River View - 3 Bedroom
Marina

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (20 reviews)
"Yes she was welcoming "
United States
Garry B.
The price is ￥16,980
￥44,163 total
includes taxes & fees
Feb 12 - Feb 13
Historic Chesapeake City Stay
Interior

Cozy loft above ink shop

Cozy loft above ink shop
Bear
9.8 out of 10, Exceptional, (7 reviews)
"Host was extremely responsive, place was in a great location for the lacrosse tournament we played in. Plenty of room, everything was great."
United States
Jeffrey R.
The price is ￥14,150
￥17,931 total
includes taxes & fees
Feb 10 - Feb 11
Cozy loft above ink shop
Fridge, microwave, oven, stovetop

Entire two-unit four-story townhouse, for multi-family vacations; free parking

Entire two-unit four-story townhouse, for multi-family vacations; free parking
Downtown Wilmington
9.6 out of 10, Exceptional, (11 reviews)
"Good place to stay, well kept, spacious and updated. "
United States
Kevin L.
The price is ￥76,409
￥125,740 total
includes taxes & fees
Feb 10 - Feb 11
Entire two-unit four-story townhouse, for multi-family vacations; free parking
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, (8 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is ￥18,866
￥25,331 total
includes taxes & fees
Feb 10 - Feb 11
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Interior

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Elkton
8.6 out of 10, Excellent, (14 reviews)
"Nice and quiet place to stay"
United States
Gary M.
The price is ￥21,225
￥44,663 total
includes taxes & fees
Feb 10 - Feb 11
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
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

Bally's Dover Casino Resort

Bally's Dover Casino Resort

10/10 Excellent
"All was well ! Will stay again !"
Miah 1-night trip
Posted 2 days ago
Bally's Dover Casino Resort

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:

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

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?

Chesapeake Bay House with Dock & Private Beach: This vacation home rental near Middletown is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 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 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.