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

Holiday Homes in Chesapeake City

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Our top choices for Chesapeake City holiday homes

1. 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 NZ$493
includes taxes & fees
3 Nov - 4 Nov
Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure

2. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
8.0 out of 10, Very good, (1 review)
The price is NZ$972
includes taxes & fees
10 Nov - 11 Nov
Bohemia Manor Farm

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)
"Wonderful spot for five ladies to enjoy an evening away close to Chesapeake City"
United States
Rebecca G.
The price is NZ$645
includes taxes & fees
3 Nov - 4 Nov
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

4. 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 NZ$686
includes taxes & fees
1 Dec - 2 Dec
Elegant Family Stay • Quiet Neighborhood • Comfort

5. 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, (5 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$731
includes taxes & fees
9 Nov - 10 Nov
Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge

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, (165 reviews)
"Family friendly, clean, quiet and great place to relax and watch the birds."
United States
Teresa M.
The price is NZ$898
includes taxes & fees
16 Nov - 17 Nov
5-bedroom vacation home 5 minutes from historic Charlestown

7. 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)
"Matt was a wonderful host whi responded to my texts very quickly. The house was perfect for a quick getaway celebrating my dad's retirement. Fishing from the dock was a plus, and everyone caught fish, even some "keepers"."
United States
Joe M.
The price is NZ$899
includes taxes & fees
4 Nov - 5 Nov
Waterfront house with amazing views. Top of the Chesapeake

8. 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 NZ$632
includes taxes & fees
8 Nov - 9 Nov
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..

9. 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, (3 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 NZ$352
includes taxes & fees
3 Nov - 4 Nov
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland

10. 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 NZ$170
includes taxes & fees
4 Nov - 5 Nov
Charming 2-bedroom house in Aberdeen with WiFi and AC

11. 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$380
includes taxes & fees
2 Dec - 3 Dec
Amish Countryside Escape at Forest Edge Farm

12. 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, (18 reviews)
"Absolutely amazing stay. Host is extremely responsive and the property is incredible. Highly recommend!!"
United States
Erika R.
The price is NZ$2,483
includes taxes & fees
6 Nov - 7 Nov
Woodland Retreat at Fair Hill- Hot Tub, Pool, and Sport Court

13. Cozy 1-bedroom bungalow in quaint Darlington with AC

Cozy 1-bedroom bungalow in quaint Darlington with AC
Darlington
10.0 out of 10, Exceptional, (11 reviews)
"Excellent host, property, and experience. We enjoyed our stay, and we will be back."
United States
Kevin A.
The price is NZ$248
includes taxes & fees
1 Dec - 2 Dec
Cozy 1-bedroom bungalow in quaint Darlington with AC

14. 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 NZ$608
includes taxes & fees
30 Nov - 1 Dec
Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

15. 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 NZ$669
includes taxes & fees
12 Nov - 13 Nov
Harmony Family Estate A Beautiful 5-bedroom house in Wilmington for your group

16. 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 NZ$929
includes taxes & fees
4 Nov - 5 Nov
Charming 3-bedroom, two-living room Victorian home in Historic New Castle
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

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Chesapeake City Holiday Homes information

Number of reviews
397
Accommodation
159 Holiday Homes
Lowest Price
NZ$170
Highest Price
NZ$2,483