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 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

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.
$267 nightly
The price is $283
Aug 23 - Aug 24
Total with taxes and fees
Historic Chesapeake City Stay
Panoramic Cottage, Vineyard View | Exterior

2. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
$372 nightly
The price is $395
Aug 25 - Aug 26
Total with taxes and fees
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.
$105 nightly
The price is $111
Aug 31 - Sep 1
Total with taxes and fees
Country Get Away Studio Apartment
Property grounds

4. Sunset River Cottage

Sunset River Cottage
Elkton
9.0 out of 10, Wonderful, (23 reviews)
"The property was just what we needed. Very quiet, laid back and the pier was great for fishing!"
United States
Ray D.
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.
$285 nightly
The price is $296
Aug 23 - Aug 24
Total with taxes and fees
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
$224 nightly
The price is $233
Aug 21 - Aug 22
Total with taxes and fees
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.
$231 nightly
The price is $240
Aug 21 - Aug 22
Total with taxes and fees
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.
$388 nightly
The price is $401
Aug 26 - Aug 27
Total with taxes and fees
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.
$325 nightly
The price is $333
Aug 24 - Aug 25
Total with taxes and fees
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.
$502 nightly
The price is $526
Aug 23 - Aug 24
Total with taxes and fees
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, (13 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
$152 nightly
The price is $161
Aug 22 - Aug 23
Total with taxes and fees
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.
$342 nightly
The price is $363
Aug 24 - Aug 25
Total with taxes and fees
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Interior

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.
$376 nightly
The price is $384
Aug 23 - Aug 24
Total with taxes and fees
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
$253 nightly
The price is $278
Aug 23 - Aug 24
Total with taxes and fees
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.
$195 nightly
The price is $206
Aug 30 - Aug 31
Total with taxes and fees
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.
$560 nightly
The price is $594
Sep 16 - Sep 17
Total with taxes and fees
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.
$1,557 nightly
The price is $1,568
Sep 8 - Sep 9
Total with taxes and fees
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.
$435 nightly
The price is $480
Aug 24 - Aug 25
Total with taxes and fees
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.
$201 nightly
The price is $213
Aug 23 - Aug 24
Total with taxes and fees
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, (7 reviews)
"Enjoyed our stay."
United States
Erik H.
$384 nightly
The price is $384
Sep 16 - Sep 17
Total with taxes and fees
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

Ramada by Wyndham Newark/Wilmington

Ramada by Wyndham Newark/Wilmington

8/10 Good
"Professional, helpful staff"
Shionlaia 3-night trip
Posted less than an hour ago
Ramada by Wyndham Newark/Wilmington

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.