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

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Check prices for these dates

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

Our top choices for Chesapeake City holiday homes

A room with a bed, a dresser, a window with curtains, and an air conditioning unit.

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 £214
includes taxes & fees
30 Sept - 1 Oct
HISTORIC WATERFRONT 2 Bedrooms/4 beds in Chesapeake City with AC
A bed with white and blue pillows, a tufted headboard, and three framed botanical prints on the wall.

2. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
The price is £282
includes taxes & fees
21 Sept - 22 Sept
Bohemia Manor Farm
A modern kitchen with dark cabinets, a stainless steel refrigerator, and a wooden floor.

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 £282
includes taxes & fees
21 Sept - 22 Sept
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
A two-story residential building with a stone facade, a large front lawn, and a driveway.

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 £283
includes taxes & fees
15 Sept - 16 Sept
Elegant Family Stay • Quiet Neighborhood • Comfort
A home theater room with a curved seating area, a large flat-screen TV, and a carpeted floor.

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 £259
includes taxes & fees
14 Sept - 15 Sept
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
A lakeside view with a grassy area, a sandy beach, and a row of white chairs.

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 £387
includes taxes & fees
16 Sept - 17 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.

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 £370
includes taxes & fees
20 Sept - 21 Sept
Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge

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 £146
includes taxes & fees
9 Sept - 10 Sept
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
A living room with teal walls, a black sofa, a patterned rug, a flat-screen TV on a wooden stand, and a painting on the wall.

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 £83
includes taxes & fees
22 Sept - 23 Sept
Charming 2-bedroom house in Aberdeen with WiFi and AC
A spacious living area with a large gray sofa, a coffee table, and a bar area with stools.

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 £1,062
includes taxes & fees
14 Sept - 15 Sept
Woodland Retreat at Fair Hill- Hot Tub, Pool, and Sport Court
A living room with a dark grey sectional sofa, a round wooden coffee table, and a small side table.

11. Cozy Pet Friendly House

Cozy Pet Friendly House
Wilmington
The price is £140
includes taxes & fees
13 Sept - 14 Sept
Cozy Pet Friendly House
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 £152
includes taxes & fees
9 Sept - 10 Sept
Amish Countryside Escape at Forest Edge Farm
A room with a bed, a wooden door, a patterned rug, and a mirror.

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 £234
includes taxes & fees
11 Sept - 12 Sept
Charming 3-bedroom house in wonderful Pennsville Township with AC, WiFi
A living room with a fireplace, two sofas, a zebra rug, and a ceiling fan.

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 £296
includes taxes & fees
9 Sept - 10 Sept
Harmony Family Estate A Beautiful 5-bedroom house in Wilmington for your group
A modern living room with a grey sofa, a round coffee table, and a large horse painting on the wall.

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 £170
includes taxes & fees
12 Sept - 13 Sept
New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi
A garden with a fountain, surrounded by lush greenery and flowering plants.

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 £153
includes taxes & fees
27 Sept - 28 Sept
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

Ramada by Wyndham Newark/Wilmington

Ramada by Wyndham Newark/Wilmington

10/10 Excellent
"A week to receive your deposit back seems very unexpected and unnecessary for"
Kyle 1-night trip
Posted 1 hour ago
Ramada by Wyndham Newark/Wilmington

Find out more about Chesapeake City

Chesapeake City Holiday Homes information

Number of reviews
278
Accommodation
161 Holiday Homes
Lowest Price
£83
Highest Price
£1,062