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Our top choices for Middletown vacation homes

1. Bohemia Hideaway. Escape to a 14 acre peaceful retreat.

Bohemia Hideaway. Escape to a 14 acre peaceful retreat.
Middletown
The price is ¥39,819
¥43,823 total
includes taxes & fees
Nov 17 - Nov 18
Bohemia Hideaway. Escape to a 14 acre peaceful retreat.

2. Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure

Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
Chesapeake City
9.6 out of 10, Exceptional, (7 reviews)
"Everything was as advertised. Property is not new, but everything was clean and well cared for. Evenings on the water were peaceful and relaxing. We enjoyed our stay and definitely intend to return."
United States
John
The price is ¥30,291
¥50,700 total
includes taxes & fees
Nov 11 - Nov 12
Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure

3. Elegant Family Stay • Quiet Neighborhood • Comfort

Elegant Family Stay • Quiet Neighborhood • Comfort
New Castle
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful well kept property with lots of room to relax."
United States
Daniel J.
The price is ¥44,369
¥58,375 total
includes taxes & fees
Nov 22 - Nov 23
Elegant Family Stay • Quiet Neighborhood • Comfort

4. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
8.0 out of 10, Very good, (1 review)
The price is ¥83,761
¥88,787 total
includes taxes & fees
Nov 19 - Nov 20
Bohemia Manor Farm

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

Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
New Castle
8.4 out of 10, Very good, (24 reviews)
"I’ve stayed in much better locations."
United States
Grant H.
The price is ¥28,300
¥57,541 total
includes taxes & fees
Nov 23 - Nov 24
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..

6. 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, (7 reviews)
"Wonderful spot for five ladies to enjoy an evening away close to Chesapeake City"
United States
Rebecca G.
The price is ¥27,873
¥58,856 total
includes taxes & fees
Nov 16 - Nov 17
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

7. 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, (6 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 ¥44,191
¥69,248 total
includes taxes & fees
Nov 18 - Nov 19
Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge

8. Waterfront house with amazing views. Top of the Chesapeake

Waterfront house with amazing views. Top of the Chesapeake
Perryville
10.0 out of 10, Exceptional, (115 reviews)
"Host was very communicative."
United States
Lee Anne K.
The price is ¥39,392
¥77,264 total
includes taxes & fees
Nov 11 - Nov 12
Waterfront house with amazing views. Top of the Chesapeake

9. 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, (165 reviews)
"Family friendly, clean, quiet and great place to relax and watch the birds."
United States
Teresa M.
The price is ¥35,515
¥76,620 total
includes taxes & fees
Nov 19 - Nov 20
5-bedroom vacation home 5 minutes from historic Charlestown

10. Charming 3-bedroom, two-living room Victorian home in Historic New Castle

Charming 3-bedroom, two-living room Victorian home in Historic New Castle
Historical Old New Castle
The price is ¥45,507
¥82,949 total
includes taxes & fees
Nov 17 - Nov 18
Charming 3-bedroom, two-living room Victorian home in Historic New Castle

11. Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm
Nottingham
9.2 out of 10, Wonderful, (5 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 ¥19,751
¥32,534 total
includes taxes & fees
Nov 16 - Nov 17
Amish Countryside Escape at Forest Edge Farm

12. 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
9.4 out of 10, Exceptional, (11 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 ¥29,864
¥59,334 total
includes taxes & fees
Nov 19 - Nov 20
Harmony Family Estate A Beautiful 5-bedroom house in Wilmington for your group

13. Delightful 4-bedroom house in Carneys Point Township, near Wilmington & Philly!

Delightful 4-bedroom house in Carneys Point Township, near Wilmington & Philly!
Carneys Point Township
The price is ¥42,947
¥103,871 total
includes taxes & fees
Nov 17 - Nov 18
Delightful 4-bedroom house in Carneys Point Township, near Wilmington & Philly!

14. 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, (5 reviews)
"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 ¥36,342
¥54,726 total
includes taxes & fees
Nov 16 - Nov 17
Entire Private Wilmington Home | Sleeps 6 | 2 Baths & Parking

15. Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
Betterton
The price is ¥28,584
¥55,447 total
includes taxes & fees
Nov 30 - Dec 1
Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
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.

Learn more about Middletown

Stroll through the historic district where colonial-era buildings tell stories of the town's rich past. Nearby Thousand Acre Farm offers stunning waterfront views and local festivals where you can sample Delaware's famous peach pies.

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