A steel arch bridge over a river with surrounding trees and buildings.

Middletown Vacation Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Middletown vacation rentals

Outdoor dining

Spacious Family Home | Seats 16, Sleeps 9 | 3 Sleeping/Privacy Zones

Spacious Family Home | Seats 16, Sleeps 9 | 3 Sleeping/Privacy Zones
Middletown
The price is AED 2,310
AED 2,545 total
includes taxes & fees
7 Jul - 8 Jul
Spacious Family Home | Seats 16, Sleeps 9 | 3 Sleeping/Privacy Zones
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
The price is AED 694
AED 850 total
includes taxes & fees
28 Jun - 29 Jun
Nature's Haven Tiny Home
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.
The price is AED 694
AED 876 total
includes taxes & fees
28 Jun - 29 Jun
Tiny Home Tranquil Oasis
Exterior

Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (42 reviews)
"Perfect in every way… a great stay"
United States
Robert B.
The price is AED 257
AED 409 total
includes taxes & fees
1 Jul - 2 Jul
Country Get Away Studio Apartment
Marina

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (23 reviews)
"Cleaned, beautifully decorated, not like a rental but more like a home!"
United States
Manjetjola P.
The price is AED 397
AED 1,024 total
includes taxes & fees
28 Jun - 29 Jun
Historic Chesapeake City Stay
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, (7 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.
The price is AED 342
AED 640 total
includes taxes & fees
7 Jul - 8 Jul
Summer Rustic Camping with AC and King Bed
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.
The price is AED 499
AED 1,257 total
includes taxes & fees
7 Jul - 8 Jul
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
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, (5 reviews)
The price is AED 441
AED 685 total
includes taxes & fees
12 Jul - 13 Jul
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
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, (27 reviews)
"Property was spacious with open kitchen/living room area and 2 bedrooms with their own baths."
United States
Mark F.
The price is AED 420
AED 707 total
includes taxes & fees
6 Jul - 7 Jul
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
9.8 out of 10, Exceptional, (23 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.
The price is AED 250
AED 459 total
includes taxes & fees
30 Jun - 1 Jul
Guest Suite for up to 2 in a Victorian on the Chester River
Exterior

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
10.0 out of 10, Exceptional, (12 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is AED 441
AED 592 total
includes taxes & fees
2 Jul - 3 Jul
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
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.
The price is AED 448
AED 773 total
includes taxes & fees
30 Jun - 1 Jul
Amish Countryside Escape at Forest Edge Farm
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, (23 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 AED 711
AED 1,206 total
includes taxes & fees
6 Jul - 7 Jul
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Exterior detail

Modern 1BR in Downtown Wilmington Near Riverwalk & Restaurants

Modern 1BR in Downtown Wilmington Near Riverwalk & Restaurants
Downtown Wilmington
The price is AED 397
AED 639 total
includes taxes & fees
5 Jul - 6 Jul
Modern 1BR in Downtown Wilmington Near Riverwalk & Restaurants
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, (19 reviews)
"Comfortable place, wonderful amenities, and a gracious host. "
United States
Donald H.
The price is AED 793
AED 1,303 total
includes taxes & fees
28 Jun - 29 Jun
Two-story condo in luxury townhouse. Free parking.
Smart TV

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, (11 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
The price is AED 731
AED 985 total
includes taxes & fees
8 Jul - 9 Jul
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
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.
The price is AED 796
AED 1,802 total
includes taxes & fees
1 Jul - 2 Jul
Thunder Hill Retreat - Spacious/Deck/Hot tub
WiFi, bed sheets

Turtle Cove Room

Turtle Cove Room
Kent County
The price is AED 635
AED 770 total
includes taxes & fees
23 Jul - 24 Jul
Turtle Cove Room
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 AED 353
AED 570 total
includes taxes & fees
1 Jul - 2 Jul
Entire place with private parking
Terrace/patio

Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
Newark
9.8 out of 10, Exceptional, (6 reviews)
"Enjoyed our stay."
United States
Erik H.
The price is AED 539
AED 1,314 total
includes taxes & fees
7 Jul - 8 Jul
Private Home + 3 Bed/1.5 Bath + 2MI - 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

Sonesta Select Newark Christiana Mall

Sonesta Select Newark Christiana Mall

10/10 Excellent
"Very reasonable hotel for a nice convenient place with easy access to many places to explore. Restaurants, shopping, historical activities and easy access to Philadelphia/Baltimore as a metroplex between the two major cities. Tax free shopping is an extra bonus as well. Clean rooms that have been renovated and excellent staff, from management to cleaning employees and a pool with courtyard , fire pit and laundry services. Many amenities are available for an extra cost but it is available within the hotels. The reason why it is less expensive is because of the renovations being made for the hotel itself. The breakfast option has been discontinued because of the renovations, but it has many food places close by within a mile. Great bang for your buck!"
Cindy 2-night trip
Posted 1 hour ago
Sonesta Select Newark Christiana Mall

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 7 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.