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
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

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 ￥17,194
￥45,057 total
includes taxes & fees
Aug 29 - Aug 30
Historic Chesapeake City Stay
Panoramic Cottage, Vineyard View | Exterior

2. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
The price is ￥56,123
￥59,491 total
includes taxes & fees
Sep 21 - Sep 22
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 quiet country getaway. Setting, nature was great."
United States
JAMES V.
The price is ￥11,144
￥17,719 total
includes taxes & fees
Sep 2 - Sep 3
Country Get Away Studio Apartment
Terrace/patio

4. 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 ￥30,068
￥36,990 total
includes taxes & fees
Sep 24 - Sep 25
Nature's Haven Tiny Home
Terrace/patio

5. 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 ￥30,068
￥38,422 total
includes taxes & fees
Sep 24 - Sep 25
Tiny Home Tranquil Oasis
Interior

6. 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 ￥39,773
￥46,654 total
includes taxes & fees
Sep 24 - Sep 25
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
Exterior

7. 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, (13 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is ￥19,091
￥25,633 total
includes taxes & fees
Sep 24 - Sep 25
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Private kitchen

8. 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 ￥24,501
￥58,708 total
includes taxes & fees
Sep 7 - Sep 8
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Exterior

9. 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 ￥42,841
￥60,052 total
includes taxes & fees
Aug 30 - Aug 31
Elegant Family Stay • Quiet Neighborhood • Comfort
Dining

10. 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, (25 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 ￥31,092
￥53,347 total
includes taxes & fees
Aug 31 - Sep 1
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Terrace/patio

11. 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, (7 reviews)
"Enjoyed our stay."
United States
Erik H.
The price is ￥22,867
￥57,095 total
includes taxes & fees
Sep 1 - Sep 2
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
Interior

12. 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 ￥25,074
￥56,928 total
includes taxes & fees
Sep 25 - Sep 26
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
Beach

13. Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!

Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
Newark
The price is ￥23,781
￥29,896 total
includes taxes & fees
Aug 30 - Aug 31
Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
Beach

14. 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, (159 reviews)
"Family friendly, clean, quiet and great place to relax and watch the birds."
United States
Teresa M.
The price is ￥48,142
￥93,049 total
includes taxes & fees
Sep 2 - Sep 3
5-bedroom vacation home 5 minutes from historic Charlestown
Exterior

15. 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 ￥26,250
￥30,129 total
includes taxes & fees
Sep 24 - Sep 25
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
Exterior

16. Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.8 out of 10, Exceptional, (27 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
The price is ￥10,818
￥19,899 total
includes taxes & fees
Sep 24 - Sep 25
Guest Suite for up to 2 in a Victorian on the Chester River
Exterior

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

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (24 reviews)
"Great place to get away! Peaceful, serene with amenities to boast!"
United States
Arthur B.
The price is ￥33,728
￥76,542 total
includes taxes & fees
Sep 2 - Sep 3
Thunder Hill Retreat - Spacious/Deck/Hot tub
Living area

18. 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 ￥12,179
￥16,285 total
includes taxes & fees
Aug 31 - Sep 1
Charming 2-bedroom house in Aberdeen with WiFi and AC
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 property, with lots of history. We enjoyed our short stay."
United States
Terry R S.
The price is ￥27,920
￥33,811 total
includes taxes & fees
Aug 28 - Aug 29
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Living area

20. Cozy Pet Friendly House

Cozy Pet Friendly House
Wilmington
The price is ￥24,071
￥30,407 total
includes taxes & fees
Aug 31 - Sep 1
Cozy Pet Friendly House
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

Sonesta Select Newark Christiana Mall

Sonesta Select Newark Christiana Mall

8/10 Good
"Great staff here, the place is amidst renovations. We were on the 4th floor and the room had just been renovated , clean room. We used the pool and there were no towels. There were also no towels for my kids for showers the entire day. The poor guy working the front desk had been there almost 24 hours already and he gave us some smaller towels instead. If you are going there in the fall of 2026, expect the lobby to be a mess for renovations."
Steven 1-night trip
Posted less than an hour ago
Sonesta Select Newark Christiana Mall

Find out more about Chesapeake City

Search for holiday rentals in Chesapeake City on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesapeake City using one of the methods below:

  • View our selection of featured holiday rentals in Chesapeake City
  • Use the map to find apartments and other holiday homes in the Chesapeake City neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chesapeake City while they last

Look no further and take a look at our great range of rental properties in Chesapeake City!

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?

Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows : This Chesapeake City vacation home rental is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Other favorite homes for rent in Chesapeake City are HYDRANGEA HOUSE Waterview cozy 3-bdrm Getaway in quiet Chesapeake City AC & yard and Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!.

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.