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

Chesapeake City Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Chesapeake City vacation rentals

Marina

1. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (28 reviews)
"The rental was perfect for what we needed. The bed and living room furniture were very comfortable and the kitchen well stocked. The host was quick to respond to questions I had. I will definitely see if this rental if available the next time I’m in the area."
United States
Martha J.
The price is AED 397
AED 1,040 total
includes taxes & fees
17 Aug - 18 Aug
Historic Chesapeake City Stay
Luxury House, Multiple Bedrooms, Lake View | Interior

2. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
The price is AED 1,309
AED 1,388 total
includes taxes & fees
30 Aug - 31 Aug
Bohemia Manor Farm
Exterior

3. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (47 reviews)
"Beautiful property in a quiet location. Immaculate! Will definitely be back. "
United States
Mary S.
The price is AED 257
AED 409 total
includes taxes & fees
31 Aug - 1 Sep
Country Get Away Studio Apartment
Property grounds

4. Sunset River Cottage

Sunset River Cottage
Elkton
9.0 out of 10, Wonderful, (22 reviews)
"The property was just what we needed. Very quiet, laid back and the pier was great for fishing!"
United States
Ray D.
The price is AED 955
AED 1,581 total
includes taxes & fees
20 Aug - 21 Aug
Sunset River Cottage
Interior

5. Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail

Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
Bear
10.0 out of 10, Exceptional, (3 reviews)
"Great stay. Awesome owner. Nice restaurant right up the ramp. Would def recommend and do again if in the area!!!"
United States
Justin M.
The price is AED 918
AED 1,092 total
includes taxes & fees
19 Aug - 20 Aug
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
Terrace/patio

6. Nature's Haven Tiny Home

Nature's Haven Tiny Home
Bear
10.0 out of 10, Exceptional, (4 reviews)
"Great place to relax after a while on the go. Karin was very friendly and informative about places to see in the area. Everything was great "
United States
Maxwell
The price is AED 694
AED 865 total
includes taxes & fees
17 Aug - 18 Aug
Nature's Haven Tiny Home
Terrace/patio

7. Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
10.0 out of 10, Exceptional, (2 reviews)
"This was a stop over on our way to the beach- it was a convenient comfy space for our family."
United States
Erin C.
The price is AED 694
AED 883 total
includes taxes & fees
17 Aug - 18 Aug
Tiny Home Tranquil Oasis
Exterior

8. 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 AED 1,094
AED 1,511 total
includes taxes & fees
26 Aug - 27 Aug
Elegant Family Stay • Quiet Neighborhood • Comfort
Dining

9. Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Newark
9.6 out of 10, Exceptional, (24 reviews)
"Very nice property, just right size for our needs. Great neighborhood. Kitchen very nice, check in easy."
United States
Lori W.
The price is AED 711
AED 1,224 total
includes taxes & fees
24 Aug - 25 Aug
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Terrace/patio

10. 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 AED 1,324
AED 2,068 total
includes taxes & fees
23 Aug - 24 Aug
Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
Exterior

11. Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Elkton
10.0 out of 10, Exceptional, (12 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is AED 441
AED 592 total
includes taxes & fees
17 Aug - 18 Aug
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Coffee/tea maker, fridge, microwave, oven

12. 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 AED 536
AED 1,311 total
includes taxes & fees
25 Aug - 26 Aug
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Dining

13. 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, (18 reviews)
"I’ve stayed in much better locations."
United States
Grant H.
The price is AED 658
AED 1,411 total
includes taxes & fees
18 Aug - 19 Aug
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
Beach

14. Perfect for Groups! | Pool + Gym + Free Breakfast

Perfect for Groups! | Pool + Gym + Free Breakfast
Newark
The price is AED 875
AED 1,109 total
includes taxes & fees
19 Aug - 20 Aug
Perfect for Groups! | Pool + Gym + Free Breakfast
Smart TV

15. Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Havre de Grace
10.0 out of 10, Exceptional, (12 reviews)
"Very cool place, walking distance to everything."
United States
Brett S.
The price is AED 714
AED 979 total
includes taxes & fees
18 Aug - 19 Aug
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Sun loungers, beach towels

16. 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, (157 reviews)
"Family friendly, clean, quiet and great place to relax and watch the birds."
United States
Teresa M.
The price is AED 1,197
AED 2,250 total
includes taxes & fees
16 Sep - 17 Sep
5-bedroom vacation home 5 minutes from historic Charlestown
Smart TV, fireplace, foosball, table tennis

17. 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 AED 3,416
AED 5,832 total
includes taxes & fees
8 Sep - 9 Sep
Woodland Retreat at Fair Hill- Hot Tub, Pool, and Sport Court
Exterior

18. Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (24 reviews)
"Everything was good. Had a great time."
United States
Todd H.
The price is AED 811
AED 1,868 total
includes taxes & fees
17 Aug - 18 Aug
Thunder Hill Retreat - Spacious/Deck/Hot tub
Exterior

19. Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Port Deposit
9.8 out of 10, Exceptional, (51 reviews)
"Very unique and cozy property close to everything we needed. "
United States
John H.
The price is AED 645
AED 777 total
includes taxes & fees
17 Aug - 18 Aug
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Terrace/patio

20. Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
Newark
9.8 out of 10, Exceptional, (6 reviews)
"Enjoyed our stay."
United States
Erik H.
The price is AED 567
AED 1,357 total
includes taxes & fees
16 Sep - 17 Sep
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
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

Embassy Suites by Hilton Newark Wilmington South

Embassy Suites by Hilton Newark Wilmington South

10/10 Excellent
"Everyone was so nice. Breakfast was great wide variety of choices. Light snacks in the evening and drink coupon was very thoughtful as well. Elevators run a little slow but all and all 10 out of 10"
Leila 2-night trip
Posted less than an hour ago
Embassy Suites by Hilton Newark Wilmington South

Frequently asked questions

Can I find vacation rentals in Chesapeake City?

Yes, you can find vacation rentals close to popular local attractions in Chesapeake City, or you can select a more secluded option if you want a relaxing place to stay. Chesapeake City is known for its restaurants and waterfront. Make sure you have time to check out the museums while you're in the area.

What are some of the best vacation rentals in Chesapeake City?

HYDRANGEA HOUSE Waterview cozy 3-bdrm Getaway in quiet Chesapeake City AC & yard: This Chesapeake City vacation home rental is located on a river and has a patio, a selection of books, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Another good choice for your trip to Chesapeake City is Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows .

How many vacation rentals are there in Chesapeake City?

With 11 Expedia vacation rentals, you're sure to find just the right place for your Chesapeake City stay.

What can I see and do in Chesapeake City?

Cultural attractions include C and D Canal Museum, whereas Canal Wildlife Management Area is a spot to enjoy nature. While here, Chesapeake Inn Marina and Chesapeake City Docks are other places worth a visit.

What are vacation rentals like in Chesapeake City?

Vacation rentals are privately owned properties you can book for a few days or a quick weekend in Chesapeake City. Vacation rentals feature extras like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for small groups.