Chesapeake City Vacation Rentals

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Jan 6 - Jan 7
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Jan 7 - Jan 8
This weekend
Jan 9 - Jan 11
Next weekend
Jan 16 - Jan 18

Our top choices for Chesapeake City vacation rentals

Marina
Historic Chesapeake City Stay

Cabin in Chesapeake City

Historic Chesapeake City Stay
9.0 out of 10, Wonderful, (20)
"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 8 - Jan 9
Total with taxes and fees
Historic Chesapeake City Stay
Smart TV, foosball, books
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

Apartment in Chesapeake City

Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
2.0 star property
9.4 out of 10, Exceptional, (3)
"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 8 - Jan 9
Total with taxes and fees
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
Exterior
Country Get Away 1 Bedroom Apartment

Apartment in Elkton

Country Get Away 1 Bedroom Apartment
9.8 out of 10, Exceptional, (40)
"Absolutely love the accommodations. First impression when entering room was so fresh and clean."
United States
Beverly M.
$105 nightly
The price is $111
Jan 13 - Jan 14
Total with taxes and fees
Country Get Away 1 Bedroom Apartment
Property grounds
New Construction townhome close to everything downtown w/transparent pricing

Vacation Home in Hilltop

New Construction townhome close to everything downtown w/transparent pricing
9.6 out of 10, Exceptional, (23)
"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.
$158 nightly
The price is $163
Jan 18 - Jan 19
Total with taxes and fees
New Construction townhome close to everything downtown w/transparent pricing
Interior
Cozy loft above ink shop

Apartment in Bear

Cozy loft above ink shop
9.8 out of 10, Exceptional, (6)
"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 8 - Jan 9
Total with taxes and fees
Cozy loft above ink shop
Smart TV
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

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)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
$152 nightly
The price is $161
Jan 8 - Jan 9
Total with taxes and fees
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Exterior
Guest Suite for up to 2 in a Victorian on the Chester River

Apartment in Millington

Guest Suite for up to 2 in a Victorian on the Chester River
9.6 out of 10, Exceptional, (19)
"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
Jan 13 - Jan 14
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
1 bedroom
Summer Rustic Camping with AC and King Bed

Vacation Home in Elkton

Summer Rustic Camping with AC and King Bed
9.6 out of 10, Exceptional, (5)
"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.
$155 nightly
The price is $156
Jan 8 - Jan 9
Total with taxes and fees
Summer Rustic Camping with AC and King Bed
Interior
Private 3 room Queen Suite w/Kitchenette

Apartment in Port Deposit

Private 3 room Queen Suite w/Kitchenette
10.0 out of 10, Exceptional, (29)
"Perfect location for that town. "
United States
Hisham M.
$235 nightly
The price is $249
Jan 8 - Jan 9
Total with taxes and fees
Private 3 room Queen Suite w/Kitchenette
Terrace/patio
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

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)
"Enjoyed our stay."
United States
Erik H.
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
Exterior
Thunder Hill Retreat - Spacious/Deck/Hot tub

Cottage in Lincoln University

Thunder Hill Retreat - Spacious/Deck/Hot tub
10.0 out of 10, Exceptional, (17)
"Grat time"
United States
Wanda B.
$404 nightly
The price is $446
Jan 12 - Jan 13
Total with taxes and fees
Thunder Hill Retreat - Spacious/Deck/Hot tub
Fridge, microwave, oven, stovetop
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Vacation Home in Elkton

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
10.0 out of 10, Exceptional, (2)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
$322 nightly
The price is $341
Jan 8 - Jan 9
Total with taxes and fees
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Private kitchen
A Cool Place to Stay in Wilmington DE

Vacation Home in Wilmington

A Cool Place to Stay in Wilmington DE
$150 nightly
The price is $155
Jan 8 - Jan 9
Total with taxes and fees
A Cool Place to Stay in Wilmington DE
Smart TV, books
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Cottage in Port Deposit

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
10.0 out of 10, Exceptional, (34)
"What a cozy place to stay! The best part was in the morning when you can see the beautiful morning sky from the bed in the loft, the sun eloquently shining in through the windows and the deer frolicking in the yard. Comfy beds and plenty of lighting, would love to stay again."
United States
Bobbijo B.
$199 nightly
The price is $210
Jan 9 - Jan 10
Total with taxes and fees
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Outdoor dining
Free Breakfast. Pool. 10 Min Drive to the University of Delaware!

Condo in Newark

Free Breakfast. Pool. 10 Min Drive to the University of Delaware!
2.0 star property
$235 nightly
The price is $257
Feb 1 - Feb 2
Total with taxes and fees
Free Breakfast. Pool. 10 Min Drive to the University of Delaware!
Exterior detail
Time for a re-set at this Farmette in the heart of southern Chester county!

Vacation Home in Landenberg

Time for a re-set at this Farmette in the heart of southern Chester county!
2.0 star property
10.0 out of 10, Exceptional, (16)
"This is a lovely place, and we had a wonderful time. "
United States
Jonathan L.
$470 nightly
The price is $519
Jan 15 - Jan 16
Total with taxes and fees
Time for a re-set at this Farmette in the heart of southern Chester county!
Smart TV
Spacious 4-bedroom house with backyard oasis

Vacation Home in Middletown

Spacious 4-bedroom house with backyard oasis
10.0 out of 10, Exceptional, (1)
"We had a nice stay at this gorgeous house! Very comfortable and nicely appointed."
United States
Jordan K.
$1,116 nightly
The price is $1,138
Jan 13 - Jan 14
Total with taxes and fees
Spacious 4-bedroom house with backyard oasis
Interior
JVA LUXURY HOUSING

Vacation Home in Smyrna

JVA LUXURY HOUSING
10.0 out of 10, Exceptional, (1)
"The house was clean and wonderful. I highly recommend!"
United States
Daryl C.
$571 nightly
The price is $589
Jan 14 - Jan 15
Total with taxes and fees
JVA LUXURY HOUSING
Interior
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Vacation Home in Elkton

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
8.6 out of 10, Excellent, (14)
"Nice and quiet place to stay"
United States
Gary M.
$265 nightly
The price is $281
Jan 11 - Jan 12
Total with taxes and fees
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
TV, fireplace
Long Beach Cottage, (romantic couple’s getaway)

Cottage in Charlestown

Long Beach Cottage, (romantic couple’s getaway)
10.0 out of 10, Exceptional, (4)
"Loved the property and the decor. Very well done and luxurious!"
United States
Elisheva K.
$455 nightly
The price is $476
Jan 12 - Jan 13
Total with taxes and fees
Long Beach Cottage, (romantic couple’s getaway)
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

Holiday Inn Express & Suites Wilmington-Newark by IHG

Holiday Inn Express & Suites Wilmington-Newark by IHG

10/10 Excellent
"Courteous staff. Room and facility were very clean. I wasn’t thrilled about having to give a $100 deposit for “incidentals”. It seems excessive. "
Christopher 1-night trip
Posted 6 hours ago
Holiday Inn Express & Suites Wilmington-Newark by IHG

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 $125 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 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 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.