A river with a bridge, marina, and residential area.

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Chesapeake City vacation homes

2 bedrooms, iron/ironing board, WiFi (free), bed sheets

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 ￥22,198
￥44,282 total
includes taxes & fees
Sep 30 - Oct 1
HISTORIC WATERFRONT 2 Bedrooms/4 beds in Chesapeake City with AC
Luxury House, Multiple Bedrooms, Lake View | Laptop workspace, WiFi (free)

2. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
The price is ￥55,347
￥58,668 total
includes taxes & fees
Sep 23 - Sep 24
Bohemia Manor Farm
Coffee/tea maker, fridge, microwave, oven

3. 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 ￥25,943
￥58,709 total
includes taxes & fees
Sep 21 - Sep 22
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Exterior

4. 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 ￥41,482
￥57,376 total
includes taxes & fees
Sep 10 - Sep 11
Elegant Family Stay • Quiet Neighborhood • Comfort
Interior

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
8.0 out of 10, Very Good, (20 reviews)
"I’ve stayed in much better locations."
United States
Grant H.
The price is ￥24,211
￥54,354 total
includes taxes & fees
Oct 6 - Oct 7
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
Sun loungers, beach towels

6. 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, (161 reviews)
"Family friendly, clean, quiet and great place to relax and watch the birds."
United States
Teresa M.
The price is ￥41,343
￥83,202 total
includes taxes & fees
Sep 16 - Sep 17
5-bedroom vacation home 5 minutes from historic Charlestown
TV, books

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, (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 ￥48,231
￥77,323 total
includes taxes & fees
Sep 20 - Sep 21
Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
Exterior

8. Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland

Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
Port Deposit
10.0 out of 10, Exceptional, (2 reviews)
"Renee & Pat were excellent hosts and we will definitely try to book again when in the area. Everything was as advertised and much more. Being pet friendly was a plus. We enjoyed two restaurants in the area while there, Lee's Landing and Old South Smokehouse, highly recommend!"
United States
Don S.
The price is ￥26,286
￥29,708 total
includes taxes & fees
Sep 11 - Sep 12
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
TV

9. Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.6 out of 10, Good, (19 reviews)
"Nice place"
United States
christine
The price is ￥12,764
￥16,798 total
includes taxes & fees
Sep 22 - Sep 23
Charming 2-bedroom house in Aberdeen with WiFi and AC
Smart TV, fireplace, foosball, table tennis

10. 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, (14 reviews)
"Everything was as advertised, clean, neat & spacious. Great communicators and readily available to answer questions."
United States
Gary S.
The price is ￥128,684
￥227,677 total
includes taxes & fees
Sep 15 - Sep 16
Woodland Retreat at Fair Hill- Hot Tub, Pool, and Sport Court
TV, books, stereo

11. Cozy Pet Friendly House

Cozy Pet Friendly House
Wilmington
The price is ￥22,891
￥28,854 total
includes taxes & fees
Sep 16 - Sep 17
Cozy Pet Friendly House
Outdoor dining

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 ￥19,269
￥33,374 total
includes taxes & fees
Sep 10 - Sep 11
Amish Countryside Escape at Forest Edge Farm
Interior

13. 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 ￥30,830
￥46,563 total
includes taxes & fees
Sep 17 - Sep 18
Charming 3-bedroom house in wonderful Pennsville Township with AC, WiFi
Smart TV, fireplace, DVD player, books

14. 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
9.0 out of 10, Wonderful, (8 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 ￥31,909
￥63,559 total
includes taxes & fees
Sep 10 - Sep 11
Harmony Family Estate A Beautiful 5-bedroom house in Wilmington for your group
Interior

15. 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 ￥21,504
￥35,575 total
includes taxes & fees
Sep 12 - Sep 13
New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi
Property grounds

16. 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 ￥18,868
￥30,816 total
includes taxes & fees
Sep 27 - Sep 28
New Construction townhome close to everything downtown w/transparent pricing
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 Chesapeake City Hotel Reviews

Comfort Inn & Suites Newark - Wilmington

Comfort Inn & Suites Newark - Wilmington

10/10 Excellent
"The rooms were very clean and comfortable bed! Bathroom had everything you needed for your stay. The lobby and dining area small but comfortable. Fireplace near. Breakfast was ok,everyone seemed to be enjoy and the staff was ever so pleasant. Check in easy breezy no issues whatsoever! Would definitely stay here again on my next visit to Delaware."
michelle 1-night trip
Posted 9 hours ago
Comfort Inn & Suites Newark - Wilmington

Find out more about Chesapeake City

Chesapeake City Vacation Homes information

Number of reviews
278
Accommodation
161 Vacation Homes
Lowest Price
￥16,798
Highest Price
￥227,677