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

Search Vacation Homes in Middletown

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sep - 27 Sep
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Middletown vacation homes

Coffee/tea maker, fridge, microwave, oven

1. 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
9.6 out of 10, Exceptional, (5 reviews)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is AED 522
AED 1,286 total
includes taxes & fees
3 Aug - 4 Aug
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
TV, computer monitors

2. Dover Home Base: 3 Mi to Motor Speedway!

Dover Home Base: 3 Mi to Motor Speedway!
Dover
9.0 out of 10, Wonderful, (7 reviews)
"Great property in a quiet neighborhood. Owner communicated easily and effectively. "
United States
Patrick C.
The price is AED 309
AED 1,616 total
includes taxes & fees
2 Aug - 3 Aug
Dover Home Base: 3 Mi to Motor Speedway!
Property grounds

3. Sunset River Cottage

Sunset River Cottage
Elkton
8.8 out of 10, Excellent, (19 reviews)
"The property was just what we needed. Very quiet, laid back and the pier was great for fishing!"
United States
Ray D.
Sunset River Cottage
Dining

4. 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, (24 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 812
AED 1,307 total
includes taxes & fees
24 Aug - 25 Aug
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
TV, books, stereo

5. Cozy House in a Quiet Neighborhood

Cozy House in a Quiet Neighborhood
Wilmington
The price is AED 545
AED 684 total
includes taxes & fees
9 Aug - 10 Aug
Cozy House in a Quiet Neighborhood
Interior

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

Charming 3-bedroom house in wonderful Pennsville Township with AC, WiFi
Pennsville Township
The price is AED 735
AED 1,154 total
includes taxes & fees
2 Aug - 3 Aug
Charming 3-bedroom house in wonderful Pennsville Township with AC, WiFi
Property grounds

7. Sunset River Shack -amazing waterfront view

Sunset River Shack -amazing waterfront view
Elkton
9.6 out of 10, Exceptional, (7 reviews)
"The home is nice The view from the deck was wonderful But there wasn’t access to the water Easy to find and we really enjoyed the area"
United States
Hope D.
The price is AED 1,008
AED 1,637 total
includes taxes & fees
3 Aug - 4 Aug
Sunset River Shack -amazing waterfront view
Property grounds

8. 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, (29 reviews)
"There were 3 of us ladies for the week. Lisa was a great host and recommendations were all perfect. We will definitely be back. Everything was clean and neat. We loved staying there. "
United States
Bonnie W.
The price is AED 443
AED 735 total
includes taxes & fees
2 Aug - 3 Aug
New Construction townhome close to everything downtown w/transparent pricing
Outdoor spa tub

9. Sailor's Sunrise Cottage - Chesapeake Bay

Sailor's Sunrise Cottage - Chesapeake Bay
Perryville
9.2 out of 10, Wonderful, (60 reviews)
"Great location for a girls getaway!"
United Kingdom
Jennifer T.
Sailor's Sunrise Cottage - Chesapeake Bay
Outdoor dining

10. 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 500
AED 836 total
includes taxes & fees
24 Aug - 25 Aug
Amish Countryside Escape at Forest Edge Farm
Smart TV, fireplace, DVD player, books

11. Harmony Family Estate A Beautiful 5-bedroom house in Wilmington for your group

Harmony Family Estate A Beautiful 5-bedroom house in Wilmington for your group
Wilmington
9.6 out of 10, Exceptional, (5 reviews)
"We very much enjoyed resting in the house between our activities. The kids loved the large room for watching a soccer match. The dining area is exceptionally nice for kids."
United States
Emily M.
The price is AED 826
AED 1,602 total
includes taxes & fees
9 Aug - 10 Aug
Harmony Family Estate A Beautiful 5-bedroom house in Wilmington for your group
Private kitchen

12. Entire Private Wilmington Home | Sleeps 6 | 2 Baths & Parking

Entire Private Wilmington Home | Sleeps 6 | 2 Baths & Parking
Wilmington
10.0 out of 10, Exceptional, (1 review)
"The property is very clean, recently updated and had more than enough room for the four of us staying. There was even an extra bedroom with 2 twin beds we didn't need. The neighborhood was super quiet and perfect to come back to after long days of adventure in the area."
United States
Grant S.
The price is AED 760
AED 1,232 total
includes taxes & fees
3 Aug - 4 Aug
Entire Private Wilmington Home | Sleeps 6 | 2 Baths & Parking
Interior

13. New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi

New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi
Hilltop
The price is AED 532
AED 876 total
includes taxes & fees
12 Aug - 13 Aug
New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi
Smart TV, fireplace, foosball, table tennis

14. Woodland Retreat at Fair Hill- Hot Tub, Pool, and Sport Court

Woodland Retreat at Fair Hill- Hot Tub, Pool, and Sport Court
Elkton
10.0 out of 10, Exceptional, (12 reviews)
"Everything was as advertised, clean, neat & spacious. Great communicators and readily available to answer questions."
United States
Gary S.
The price is AED 3,846
AED 6,328 total
includes taxes & fees
20 Aug - 21 Aug
Woodland Retreat at Fair Hill- Hot Tub, Pool, and Sport Court
Coffee/tea maker, fridge, microwave, oven

15. 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 AED 2,033
AED 3,146 total
includes taxes & fees
5 Aug - 6 Aug
Entire two-unit four-story townhouse, for multi-family vacations; free parking
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

Bally's Dover Casino Resort

Bally's Dover Casino Resort

10/10 Excellent
"Great steak house"
Carol 1-night trip
Posted 3 hours ago
Bally's Dover Casino Resort