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

Holiday Homes in Middletown

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Middletown holiday homes

A kitchen with wooden cabinets, a microwave, a stove, and a coffee maker.

1. HISTORIC WATERFRONT 2 Bedrooms/4 beds in Chesapeake City with AC

HISTORIC WATERFRONT 2 Bedrooms/4 beds in Chesapeake City with AC
Chesapeake City
10.0 out of 10, Exceptional, (2 reviews)
"A charming cottage with an amazing backyard overlooking the canal. Communication was exceptional."
United States
Deb D.
The price is NZ$507
includes taxes & fees
21 Oct - 22 Oct
HISTORIC WATERFRONT 2 Bedrooms/4 beds in Chesapeake City with AC
A bunk bed room with white bedding and blue throw blankets.

2. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
The price is NZ$640
includes taxes & fees
26 Oct - 27 Oct
Bohemia Manor Farm
A two-story residential building with a stone facade, a large front lawn, and a driveway.

3. Elegant Family Stay • Quiet Neighborhood • Comfort

Elegant Family Stay • Quiet Neighborhood • Comfort
New Castle
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful well kept property with lots of room to relax."
United States
Daniel J.
The price is NZ$626
includes taxes & fees
1 Oct - 2 Oct
Elegant Family Stay • Quiet Neighborhood • Comfort
A home theater room with a curved seating area, a large flat-screen TV, and a carpeted floor.

4. Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..

Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
New Castle
8.0 out of 10, Very good, (20 reviews)
"I’ve stayed in much better locations."
United States
Grant H.
The price is NZ$721
includes taxes & fees
28 Sept - 29 Sept
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
A modern kitchen with dark cabinets, a stainless steel refrigerator, and a wooden floor.

5. 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
9.8 out of 10, Exceptional, (6 reviews)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is NZ$634
includes taxes & fees
29 Sept - 30 Sept
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
A garden with a fountain, surrounded by lush greenery and flowering plants.

6. 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)
"We love this townhouse, close to everything!"
United States
Judy P.
The price is NZ$353
includes taxes & fees
27 Sept - 28 Sept
New Construction townhome close to everything downtown w/transparent pricing

7. Sunset River Shack -amazing waterfront view

Sunset River Shack -amazing waterfront view
Elkton
9.6 out of 10, Exceptional, (13 reviews)
"This is our 3rd year in a row renting Jessica’s property. We truly enjoyed our stay. Highly recommend staying here. Beautiful backyard looking out to the bay! It has been a highlight staying here visiting for UD graduations. We hope to be back!"
United States
Natasha G.
The price is NZ$806
includes taxes & fees
8 Oct - 9 Oct
Sunset River Shack -amazing waterfront view
A living room with a dark grey sectional sofa, a round wooden coffee table, and a small side table.

8. Cozy, Comfortable, Pet Friendly Home with a fenced in private yard

Cozy, Comfortable, Pet Friendly Home with a fenced in private yard
Wilmington
10.0 out of 10, Exceptional, (1 review)
"Spotless and so cozy. It was like coming home. Our host was communicative and kind. We’d love to come back."
United States
Chris D.
The price is NZ$347
includes taxes & fees
8 Oct - 9 Oct
Cozy, Comfortable, Pet Friendly Home with a fenced in private yard
A living room with a fireplace, two sofas, a zebra rug, and a ceiling fan.

9. 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
9.2 out of 10, Wonderful, (9 reviews)
"Comfy cozy… home away from home. Location was perfectly centered for the activities we did and the restaurants we chose. Beds and sheets were great and plenty of hot water. We had a nice relaxing stay."
United States
carla k.
The price is NZ$728
includes taxes & fees
27 Sept - 28 Sept
Harmony Family Estate A Beautiful 5-bedroom house in Wilmington for your group
A lakeside view with a grassy area, a sandy beach, and a row of white chairs.

10. 5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
9.8 out of 10, Exceptional, (163 reviews)
"Family friendly, clean, quiet and great place to relax and watch the birds."
United States
Teresa M.
The price is NZ$908
includes taxes & fees
29 Sept - 30 Sept
5-bedroom vacation home 5 minutes from historic Charlestown
A spacious room with a large sliding glass door leading to a deck, a dining area with a white table, and a cozy seating area with a view of the water.

11. Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge

Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
Charlestown
10.0 out of 10, Exceptional, (3 reviews)
"Had a wonderful stay. They really thought of everything. Had everything we could have possibly needed. It's a beautiful place and it was very clean and cared for."
United States
Laura K.
The price is NZ$885
includes taxes & fees
29 Sept - 30 Sept
Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
A patio with a table and chairs, an umbrella, and a view of a grassy yard and trees.

12. Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm
Nottingham
9.0 out of 10, Wonderful, (4 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 NZ$412
includes taxes & fees
26 Oct - 27 Oct
Amish Countryside Escape at Forest Edge Farm
A kitchen with white cabinets, a dishwasher, a window with a view of greenery, and a door with a glass panel.

13. 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, (3 reviews)
"Thank you for a lovely stay. Loved the reading nook. Plenty of space in this quiet, yet convenient neighborhood."
United States
Alan B.
The price is NZ$635
includes taxes & fees
26 Oct - 27 Oct
Entire Private Wilmington Home | Sleeps 6 | 2 Baths & Parking
A modern living room with a grey sofa, a round coffee table, and a large horse painting on the wall.

14. 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
10.0 out of 10, Exceptional, (2 reviews)
"If you are visiting the Chase fieldhouse for an event it is 10 minutes driving which is very convenient. The host was very accommodating for what me and my family needed. There was enough space for 5 of us to sleep comfortable."
United States
Alexis O.
The price is NZ$379
includes taxes & fees
27 Sept - 28 Sept
New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi
A spacious living area with a large gray sofa, a coffee table, and a bar area with stools.

15. 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, (15 reviews)
"Everything was as advertised, clean, neat & spacious. Great communicators and readily available to answer questions."
United States
Gary S.
The price is NZ$2,577
includes taxes & fees
9 Oct - 10 Oct
Woodland Retreat at Fair Hill- Hot Tub, Pool, and Sport Court
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

Hilton Wilmington/Christiana

Hilton Wilmington/Christiana

10/10 Excellent
"In House customer service"
abraham 2-night trip
Posted 15 hours ago
Hilton Wilmington/Christiana

Find out more about Middletown

Middletown Holiday Homes information

Number of reviews
278
Accommodation
185 Holiday Homes
Lowest Price
NZ$347
Highest Price
NZ$2,577