Aerial panorama of Chesapeake City Maryland historic fishing town on the Chesapeake Delaware canal with private boats docked in the marina and the Chesapeake City Bridge over the back creek

Chesapeake City Vacation Rentals

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sep - 13 Sep
In four months
9 Oct - 11 Oct

Our top choices for Chesapeake City vacation rentals

Marina

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (22 reviews)
"Cleaned, beautifully decorated, not like a rental but more like a home!"
United States
Manjetjola P.
The price is SAR 405
SAR 1,035 total
includes taxes & fees
22 Jun - 23 Jun
Historic Chesapeake City Stay
Interior

Charming 3-bedroom house in wonderful Pennsville Township with AC, WiFi

Charming 3-bedroom house in wonderful Pennsville Township with AC, WiFi
Pennsville Township
The price is SAR 751
SAR 1,171 total
includes taxes & fees
22 Jun - 23 Jun
Charming 3-bedroom house in wonderful Pennsville Township with AC, WiFi
Smart TV, books

The Penthouse Flat - 3bd/1ba, Laundry, Pet-Friendly

The Penthouse Flat - 3bd/1ba, Laundry, Pet-Friendly
Pennsville Township
The price is SAR 1,032
SAR 2,698 total
includes taxes & fees
22 Jun - 23 Jun
The Penthouse Flat - 3bd/1ba, Laundry, Pet-Friendly
Property grounds

New Construction townhome close to everything downtown w/transparent pricing

New Construction townhome close to everything downtown w/transparent pricing
Hilltop
9.8 out of 10, Exceptional, (27 reviews)
"Property was spacious with open kitchen/living room area and 2 bedrooms with their own baths."
United States
Mark F.
The price is SAR 429
SAR 722 total
includes taxes & fees
6 Jul - 7 Jul
New Construction townhome close to everything downtown w/transparent pricing
Exterior

Elegant Family Stay • Quiet Neighborhood • Comfort

Elegant Family Stay • Quiet Neighborhood • Comfort
New Castle
10.0 out of 10, Exceptional, (9 reviews)
"Place was super nice, and beautiful. Owners very responsive. My only thing was not coffee maker so if you are a coffee drinker bring coffee pot lol. Other then that place it absolutely beautiful "
United States
vincent
The price is SAR 1,010
SAR 1,408 total
includes taxes & fees
26 Jun - 27 Jun
Elegant Family Stay • Quiet Neighborhood • Comfort
Interior

New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi

New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi
Hilltop
The price is SAR 488
SAR 810 total
includes taxes & fees
14 Jul - 15 Jul
New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi
Fridge, microwave, oven, stovetop

Cozy Pet Friendly House in a Quiet Neighborhood Outside the City of Wilmington

Cozy Pet Friendly House in a Quiet Neighborhood Outside the City of Wilmington
Wilmington
The price is SAR 591
SAR 768 total
includes taxes & fees
7 Jul - 8 Jul
Cozy Pet Friendly House in a Quiet Neighborhood Outside the City of Wilmington
Outdoor dining

Spacious Family Home | Seats 16, Sleeps 9 | 3 Sleeping/Privacy Zones

Spacious Family Home | Seats 16, Sleeps 9 | 3 Sleeping/Privacy Zones
Middletown
The price is SAR 2,360
SAR 2,608 total
includes taxes & fees
24 Jun - 25 Jun
Spacious Family Home | Seats 16, Sleeps 9 | 3 Sleeping/Privacy Zones
Terrace/patio

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 SAR 709
SAR 869 total
includes taxes & fees
22 Jun - 23 Jun
Nature's Haven Tiny Home
Terrace/patio

Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
10.0 out of 10, Exceptional, (1 review)
"This unit is located behind a mansion /b&b. Had what we needed, clean, easy to access and Karin was helpful."
United States
Megan M.
The price is SAR 709
SAR 888 total
includes taxes & fees
22 Jun - 23 Jun
Tiny Home Tranquil Oasis
Beach

Free Breakfast. Pool. 10 Min Drive to the University of Delaware!

Free Breakfast. Pool. 10 Min Drive to the University of Delaware!
Newark
The price is SAR 877
SAR 1,102 total
includes taxes & fees
6 Jul - 7 Jul
Free Breakfast. Pool. 10 Min Drive to the University of Delaware!
Marina

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
The price is SAR 938
SAR 1,097 total
includes taxes & fees
24 Jun - 25 Jun
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
Dining

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, (23 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 SAR 726
SAR 1,221 total
includes taxes & fees
23 Jun - 24 Jun
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Beach

Perfect for Groups! | Pool + Gym + Free Breakfast

Perfect for Groups! | Pool + Gym + Free Breakfast
Newark
The price is SAR 1,002
SAR 1,254 total
includes taxes & fees
6 Jul - 7 Jul
Perfect for Groups! | Pool + Gym + Free Breakfast
Beach

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

Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
Newark
The price is SAR 652
SAR 818 total
includes taxes & fees
6 Jul - 7 Jul
Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
Terrace/patio

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

Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
Newark
9.6 out of 10, Exceptional, (5 reviews)
"Enjoyed our stay."
United States
Erik H.
The price is SAR 624
SAR 1,424 total
includes taxes & fees
23 Jun - 24 Jun
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
Exterior

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, (23 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 SAR 255
SAR 469 total
includes taxes & fees
29 Jun - 30 Jun
Guest Suite for up to 2 in a Victorian on the Chester River
Exterior

Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (42 reviews)
"Perfect in every way… a great stay"
United States
Robert B.
The price is SAR 263
SAR 418 total
includes taxes & fees
2 Jul - 3 Jul
Country Get Away Studio Apartment
Fridge, microwave, oven, stovetop

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
10.0 out of 10, Exceptional, (3 reviews)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is SAR 507
SAR 1,265 total
includes taxes & fees
22 Jun - 23 Jun
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
1 bedroom

Summer Rustic Camping with AC and King Bed

Summer Rustic Camping with AC and King Bed
Elkton
9.8 out of 10, Exceptional, (6 reviews)
"This was a unique experience in a good way, very cool to sleep in the dome with windows to the sky and trees! Nice to know host is pet-friendly, even had paw towels and a water dish. We will bring our dog next time. The pellet stove made the rainy night and morning cozy."
United States
Deb F.
The price is SAR 281
SAR 585 total
includes taxes & fees
22 Jun - 23 Jun
Summer Rustic Camping with AC and King Bed
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

10/10 Excellent
"Thank you again for a wonderful stay at the Ramada by Wyndham Newark/Wilmington DE. The staff at this piticular hotel treat you with the utmost respect and are a phenomenal team of hard working, honest and sincere people. I would like to give special thanks to Heather, Qualaia, and Lupe for going up and beyond to make my stay even more enjoyable. See you soon as I adore this very professional ladies. 😘"
Cindy 2-night trip
Posted 16 hours ago
Ramada by Wyndham Newark/Wilmington

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?

Hook Wine & Sinker~sleeps 14 to 16 water views!!!: This Chesapeake City vacation home rental is located on a river and has a patio, an arcade game room, and air-conditioning to put you at ease in your new surroundings. It has 5 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 10 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.