Chesapeake City Vacation Rentals

Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Chesapeake City vacation rentals

Marina

Cabin in Chesapeake City

Historic Chesapeake City Stay
9.0 out of 10, Wonderful, (20 reviews)
"This place was very cute and clean, also convenient to Shaefers Marina. It was a perfect place for us to spend a weekend on the bay. "
United States
Benay N.
$263 nightly
The price is $279
Jan 25 - Jan 26
Total with taxes and fees
Historic Chesapeake City Stay
Smart TV, foosball, books

Apartment in Chesapeake City

Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
9.4 out of 10, Exceptional, (3 reviews)
"House clean ac work great on hot weekends. Great bike path near by and nice restaurants by and the river was great on bike . Not to far from Dover for race I would stay again "
United States
Wayne
$316 nightly
The price is $335
Jan 23 - Jan 24
Total with taxes and fees
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
Smart TV

Apartment in Elkton

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
2.0 star property
9.8 out of 10, Exceptional, (8 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
$152 nightly
The price is $161
Jan 23 - Jan 24
Total with taxes and fees
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Exterior

Apartment in Elkton

Country Get Away 1 Bedroom Apartment
9.8 out of 10, Exceptional, (40 reviews)
"The accommodation description is good; the actual accommodations are great, better than expected, truly a quiet country getaway with many unexpected extras. Deciding to stay here was great decision. It's done right."
United States
John L.
$105 nightly
The price is $111
Jan 29 - Jan 30
Total with taxes and fees
Country Get Away 1 Bedroom Apartment
TV

Vacation Home in Aberdeen

Charming 2-bedroom house in Aberdeen with WiFi and AC
8.0 out of 10, Very Good, (11 reviews)
"Pleasant stay"
United States
Yommali G.
$88 nightly
The price is $93
Jan 23 - Jan 24
Total with taxes and fees
Charming 2-bedroom house in Aberdeen with WiFi and AC
Exterior

Apartment in Millington

Guest Suite for up to 2 in a Victorian on the Chester River
9.6 out of 10, Exceptional, (19 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
$118 nightly
The price is $125
Feb 4 - Feb 5
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
1 bedroom

Vacation Home in Elkton

Summer Rustic Camping with AC and King Bed
9.6 out of 10, Exceptional, (5 reviews)
"The owners were very attentive to our needs, and everything was exactly as advertised. We came up for a horse show in Maryland and the convenience to the grounds was exceptional, and everything was wonderful from the privacy to the beauty of the property."
United States
Rees L.
$154 nightly
The price is $155
Jan 27 - Jan 28
Total with taxes and fees
Summer Rustic Camping with AC and King Bed
Fridge, microwave, oven, stovetop

Vacation Home in Elkton

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
10.0 out of 10, Exceptional, (2 reviews)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
$322 nightly
The price is $341
Jan 23 - Jan 24
Total with taxes and fees
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Fridge, microwave, oven, stovetop

Cottage in Port Deposit

Quarry Landing - Center of Town & River View - 3 Bedroom
10.0 out of 10, Exceptional, (11 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
$200 nightly
The price is $212
Jan 26 - Jan 27
Total with taxes and fees
Quarry Landing - Center of Town & River View - 3 Bedroom
Interior

Apartment in Bear

Cozy loft above ink shop
9.8 out of 10, Exceptional, (7 reviews)
"Cozy little place to stay that was fully stocked for a fair price compared to others in the area. Plenty of parking and quiet even with the tattoo shop below. The only thing that I would like to have had is a light on the front porch but I used my flashlight on my phone so it wasn’t too bad. I would definitely stay again."
United States
Krystle M.
$103 nightly
The price is $107
Jan 25 - Jan 26
Total with taxes and fees
Cozy loft above ink shop
Property grounds

Vacation Home in Hilltop

New Construction townhome close to everything downtown w/transparent pricing
9.6 out of 10, Exceptional, (23 reviews)
"This home was perfect! It was beautifully maintained, large rooms and equipped with everything needed during our our stay. Lisa was responsive, attentive and available for all of our questions and requests. We would definitely return to this property if we are in the Wilmington area. "
United States
Lori A.
$171 nightly
The price is $176
Jan 25 - Jan 26
Total with taxes and fees
New Construction townhome close to everything downtown w/transparent pricing
Exterior

Cottage in Lincoln University

Thunder Hill Retreat - Spacious/Deck/Hot tub
10.0 out of 10, Exceptional, (18 reviews)
"Grat time"
United States
Wanda B.
$404 nightly
The price is $446
Jan 26 - Jan 27
Total with taxes and fees
Thunder Hill Retreat - Spacious/Deck/Hot tub
Exterior

Cottage in Port Deposit

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
10.0 out of 10, Exceptional, (35 reviews)
"Very secluded quaint cottage. Lovely space. Great overnight getaway. Port Deposit was just a few minutes drive. Will definitely stay again! "
United States
Tim R.
$198 nightly
The price is $209
Jan 26 - Jan 27
Total with taxes and fees
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Interior

Vacation Home in Middletown

Heated Pool • Private Backyard • Home Theater
2.0 star property
$459 nightly
The price is $490
Jan 26 - Jan 27
Total with taxes and fees
Heated Pool • Private Backyard • Home Theater
Terrace/patio

Apartment in Newark

Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
2.0 star property
9.6 out of 10, Exceptional, (5 reviews)
"Enjoyed our stay."
United States
Erik H.
$353 nightly
The price is $353
Feb 12 - Feb 13
Total with taxes and fees
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
Interior

Vacation Home in Elkton

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
8.6 out of 10, Excellent, (14 reviews)
"Nice and quiet place to stay"
United States
Gary M.
$265 nightly
The price is $281
Jan 25 - Jan 26
Total with taxes and fees
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Outdoor dining

Condo in Newark

Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
2.0 star property
$135 nightly
The price is $148
Feb 1 - Feb 2
Total with taxes and fees
Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
Terrace/patio

Vacation Home in Kent County

High Tide Haven Suite
$195 nightly
The price is $202
Jan 23 - Jan 24
Total with taxes and fees
High Tide Haven Suite
Dining

Vacation Home in Newark

Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
9.6 out of 10, Exceptional, (21 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
Jan 29 - Jan 30
Total with taxes and fees
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Outdoor dining

Vacation Home in Nottingham

Amish Countryside Escape at Forest Edge Farm
2.0 star property
$189 nightly
The price is $190
Jan 27 - Jan 28
Total with taxes and fees
Amish Countryside Escape at Forest Edge Farm
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

Hyatt Place Wilmington Riverfront

Hyatt Place Wilmington Riverfront

10/10 Excellent
"The room was spotless and the amenities were plentiful."
MICHAEL 1-night trip
Posted 2 days ago
Hyatt Place 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 $93 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?

Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!: Visitors like this Chesapeake City vacation home rental. It 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.

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.