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
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

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, (24 reviews)
"Cleaned, beautifully decorated, not like a rental but more like a home!"
United States
Manjetjola P.
$265 nightly
The price is $281
Jul 12 - Jul 13
Total with taxes and fees
Historic Chesapeake City Stay
TV

Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.8 out of 10, Good, (17 reviews)
"Nice place"
United States
christine
$88 nightly
The price is $93
Jul 13 - Jul 14
Total with taxes and fees
Charming 2-bedroom house in Aberdeen with WiFi and AC
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.
$118 nightly
The price is $125
Jul 6 - Jul 7
Total with taxes and fees
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.
$105 nightly
The price is $111
Jul 13 - Jul 14
Total with taxes and fees
Country Get Away Studio Apartment
Exterior

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, (1 review)
"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.
$185 nightly
The price is $186
Jul 6 - Jul 7
Total with taxes and fees
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
Smart TV

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, (12 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
$152 nightly
The price is $161
Jul 6 - Jul 7
Total with taxes and fees
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Exterior

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, (48 reviews)
"Very unique and cozy property close to everything we needed. "
United States
John H.
$200 nightly
The price is $211
Jul 12 - Jul 13
Total with taxes and fees
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
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, (7 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.
$181 nightly
The price is $182
Jul 8 - Jul 9
Total with taxes and fees
Summer Rustic Camping with AC and King Bed
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, (28 reviews)
"There were 3 of us ladies for the week. Lisa was a great host and recommendations were all perfect. We will definitely be back. Everything was clean and neat. We loved staying there. "
United States
Bonnie W.
$206 nightly
The price is $211
Jul 7 - Jul 8
Total with taxes and fees
New Construction townhome close to everything downtown w/transparent pricing
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.
$322 nightly
The price is $341
Jul 9 - Jul 10
Total with taxes and fees
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
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.
$320 nightly
The price is $328
Jul 6 - Jul 7
Total with taxes and fees
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Exterior

Cozy 1-bedroom bungalow in quaint Darlington with AC

Cozy 1-bedroom bungalow in quaint Darlington with AC
Darlington
10.0 out of 10, Exceptional, (3 reviews)
"very clean and cozy host was very nice . They had everything we needed for our stay. Very convenient to all local activities. Would stay there agin when in area."
United States
Jacquelyn O.
$141 nightly
The price is $149
Aug 4 - Aug 5
Total with taxes and fees
Cozy 1-bedroom bungalow in quaint Darlington with AC
Exterior

Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (23 reviews)
"Everything was good. Had a great time."
United States
Todd H.
$482 nightly
The price is $532
Jul 13 - Jul 14
Total with taxes and fees
Thunder Hill Retreat - Spacious/Deck/Hot tub
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
$225 nightly
The price is $234
Jul 6 - Jul 7
Total with taxes and fees
Nature's Haven Tiny Home
Interior

Private 3 room Queen Suite w/Kitchenette

Private 3 room Queen Suite w/Kitchenette
Port Deposit
10.0 out of 10, Exceptional, (30 reviews)
"Perfect location for that town. "
United States
Hisham M.
$271 nightly
The price is $287
Jul 6 - Jul 7
Total with taxes and fees
Private 3 room Queen Suite w/Kitchenette
Beach nearby

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
$343 nightly
The price is $379
Jul 9 - Jul 10
Total with taxes and fees
Waterfront Retreat with Private Dock and Beach
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.
$230 nightly
The price is $239
Jul 6 - Jul 7
Total with taxes and fees
Tiny Home Tranquil Oasis
Property grounds

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Aberdeen
$171 nightly
The price is $181
Jul 6 - Jul 7
Total with taxes and fees
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Outdoor dining

Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm
Nottingham
10.0 out of 10, Exceptional, (2 reviews)
"Property was close enough to stores and restaurants if needed. House is located in the rural area of the county (very peaceful). Property had all of the necessary kitchen utensil, pots, pans, and dishes that was needed for this trip. "
United States
jckglss6 G.
$219 nightly
The price is $221
Jul 13 - Jul 14
Total with taxes and fees
Amish Countryside Escape at Forest Edge Farm
Smart TV

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)
"The house was very cozy and close to my venue Jennifer was very responsive with any questions nice place to stay roomy"
United States
Liza
$246 nightly
The price is $261
Jul 7 - Jul 8
Total with taxes and fees
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
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

Comfort Inn & Suites Newark - Wilmington

Comfort Inn & Suites Newark - Wilmington

10/10 Excellent
"Excellent staff. Q UI it and clean hotel"
Deanna 1-night trip
Posted 5 hours ago
Comfort Inn & Suites 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 $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?

Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!: This Chesapeake City vacation home rental offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, so you can cook with friends or family. It offers a patio, a garden, and a hot tub so you can immerse yourself in your vacation. Other favorite homes for rent in Chesapeake City are Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows and HYDRANGEA HOUSE Waterview cozy 3-bdrm Getaway in quiet Chesapeake City AC & yard.

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 Bay Yacht Harbour 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.