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

A riverside dock with boats, a covered seating area, and a bridge in the background.

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.
$267 nightly
The price is $283
Aug 26 - Aug 27
Total with taxes and fees
Historic Chesapeake City Stay
A brick house with a front porch, a chimney, and a well-maintained lawn.

2. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
$400 nightly
The price is $424
Sep 8 - Sep 9
Total with taxes and fees
Bohemia Manor Farm
A wooden cabin with a porch, surrounded by dense forest.

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.
$105 nightly
The price is $111
Sep 1 - Sep 2
Total with taxes and fees
Country Get Away Studio Apartment
A covered deck area with a grill and outdoor seating.

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
$224 nightly
The price is $233
Aug 26 - Aug 27
Total with taxes and fees
Nature's Haven Tiny Home

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.
$233 nightly
The price is $242
Aug 26 - Aug 27
Total with taxes and fees
Tiny Home Tranquil Oasis
A boat interior with a white leather sofa, a cushioned bench, a television, and a view of the outside.

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.
$286 nightly
The price is $297
Aug 28 - Aug 29
Total with taxes and fees
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
A residential house with a brick exterior, a dark roof, and a front porch with a bench.

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.
$152 nightly
The price is $161
Aug 26 - Aug 27
Total with taxes and fees
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
A modern kitchen with dark cabinets, a stainless steel refrigerator, and a wooden floor.

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.
$330 nightly
The price is $350
Sep 21 - Sep 22
Total with taxes and fees
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.

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.
$365 nightly
The price is $377
Aug 29 - Aug 30
Total with taxes and fees
Elegant Family Stay • Quiet Neighborhood • Comfort
A dining area with a rectangular table, red chairs, and hanging pendant lights.

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.
$325 nightly
The price is $333
Aug 26 - Aug 27
Total with taxes and fees
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
A covered outdoor seating area with a fire pit, wicker furniture, and a Netflix sign.

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.
$359 nightly
The price is $359
Sep 1 - Sep 2
Total with taxes and fees
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
A home theater room with a curved seating area, a large flat-screen TV, and a carpeted floor.

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, (19 reviews)
"I’ve stayed in much better locations."
United States
Grant H.
$352 nightly
The price is $359
Aug 27 - Aug 28
Total with taxes and fees
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
A beach with a water tower, beach umbrellas, and a hotel in the background.

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

Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
Newark
$171 nightly
The price is $188
Aug 31 - Sep 1
Total with taxes and fees
Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
A lakeside view with a grassy area, a sandy beach, and a row of white chairs.

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, (158 reviews)
"Family friendly, clean, quiet and great place to relax and watch the birds."
United States
Teresa M.
$549 nightly
The price is $582
Sep 22 - Sep 23
Total with taxes and fees
5-bedroom vacation home 5 minutes from historic Charlestown

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.
$189 nightly
The price is $190
Aug 26 - Aug 27
Total with taxes and fees
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

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.
$118 nightly
The price is $125
Sep 9 - Sep 10
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
A two-story house with a deck, a barbecue grill, and a covered patio area.

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.
$436 nightly
The price is $482
Sep 2 - Sep 3
Total with taxes and fees
Thunder Hill Retreat - Spacious/Deck/Hot tub
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.

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
$97 nightly
The price is $102
Aug 31 - Sep 1
Total with taxes and fees
Charming 2-bedroom house in Aberdeen with WiFi and AC
A stone building with a sloped roof, a picnic table, and a lighthouse with black and white stripes.

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.
$201 nightly
The price is $213
Aug 26 - Aug 27
Total with taxes and fees
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
A kitchen with a stainless steel stove, a microwave above it, and a 'HOME' sign on the wall.

20. Cozy Pet Friendly House

Cozy Pet Friendly House
Wilmington
$182 nightly
The price is $189
Sep 8 - Sep 9
Total with taxes and fees
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

Woodspring Suites Wilmington Riverfront

Woodspring Suites Wilmington Riverfront

10/10 Excellent
"Clean rooms, appliances working, nice spacious rooms, convenient parking."
Vanessa 6-night trip
Posted 14 hours ago
Woodspring Suites Wilmington Riverfront

Find out more about Chesapeake City

Everything you need to know about Chesapeake City vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesapeake City vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesapeake City vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chesapeake City vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesapeake City. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chesapeake City in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $190 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chesapeake City rentals

At Expedia, we put the best Chesapeake City vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chesapeake City rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesapeake City vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesapeake City. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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. Other favorite homes for rent in Chesapeake City are Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows 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 Bohemia Vista Marina 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.