A river with a bridge, marina, and residential area.

Chesapeake City Holiday Rentals

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Our top choices for Chesapeake City holiday rentals

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (25 reviews)
"Cleaned, beautifully decorated, not like a rental but more like a home!"
United States
Manjetjola P.
The price is AU$399
includes taxes & fees
20 July - 21 July
Historic Chesapeake City Stay

Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (43 reviews)
"Perfect in every way… a great stay"
United States
Robert B.
The price is AU$162
includes taxes & fees
23 July - 24 July
Country Get Away Studio Apartment

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 AU$181
includes taxes & fees
20 July - 21 July
Guest Suite for up to 2 in a Victorian on the Chester River

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)
"Clean and very home like. The backyard, well designed, it’s perfect to enjoy your morning coffee and a glass of wine at dinner. I will definitely come back and highly recommend this cozy place."
United States
Manjetjola P.
The price is AU$233
includes taxes & fees
24 July - 25 July
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

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.
The price is AU$271
includes taxes & fees
23 July - 24 July
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland

Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.4 out of 10, Good, (18 reviews)
"Nice place"
United States
christine
The price is AU$135
includes taxes & fees
19 July - 20 July
Charming 2-bedroom house in Aberdeen with WiFi and AC

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, (49 reviews)
"Very unique and cozy property close to everything we needed. "
United States
John H.
The price is AU$307
includes taxes & fees
23 July - 24 July
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

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
9.6 out of 10, Exceptional, (5 reviews)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is AU$489
includes taxes & fees
21 July - 22 July
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

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 AU$474
includes taxes & fees
20 July - 21 July
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

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 AU$346
includes taxes & fees
23 July - 24 July
Tiny Home Tranquil Oasis

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.
The price is AU$318
includes taxes & fees
20 July - 21 July
Amish Countryside Escape at Forest Edge Farm

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, (6 reviews)
"The little cottage was great! It was beautifully decorated which gave it charm. The location was perfect for our adventures to Conowingo Dam, antiquing in Havre De Grace and tastings of various breweries. We slept comfortably at the warm, quiet, clean bungalow. Coral was a fantastic host making sure we had everything we needed. We would definitely like to return. "
United States
Beth S.
The price is AU$216
includes taxes & fees
21 July - 22 July
Cozy 1-bedroom bungalow in quaint Darlington with AC

Private 3 room Queen Suite w/Kitchenette

Private 3 room Queen Suite w/Kitchenette
Port Deposit
10.0 out of 10, Exceptional, (32 reviews)
"Perfect location for that town. "
United States
Hisham M.
The price is AU$414
includes taxes & fees
23 July - 24 July
Private 3 room Queen Suite w/Kitchenette

New Construction townhome close to everything downtown w/transparent pricing

New Construction townhome close to everything downtown w/transparent pricing
Hilltop
9.6 out of 10, Exceptional, (29 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.
The price is AU$312
includes taxes & fees
28 July - 29 July
New Construction townhome close to everything downtown w/transparent pricing

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.
The price is AU$526
includes taxes & fees
19 July - 20 July
Waterfront Retreat with Private Dock and Beach

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
The price is AU$380
includes taxes & fees
21 July - 22 July
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

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

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Aberdeen
The price is AU$273
includes taxes & fees
20 July - 21 July
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC

Cozy House in a Quiet Neighborhood

Cozy House in a Quiet Neighborhood
Wilmington
The price is AU$272
includes taxes & fees
20 July - 21 July
Cozy House in a Quiet Neighborhood

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 AU$337
includes taxes & fees
3 Aug - 4 Aug
Nature's Haven Tiny Home

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 AU$420
includes taxes & fees
23 July - 24 July
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
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

Find out more about Chesapeake City

Everything you need to know about Chesapeake City holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesapeake City holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chesapeake City holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesapeake City holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesapeake City holiday rentals we have selected for you start as low as AU$135 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chesapeake City rentals

At Expedia, we put the best Chesapeake City holiday 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 holiday.

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. 

Frequently asked questions

Can I find holiday rentals in Chesapeake City?

Yes, there are holiday rentals close to the most popular sights in Chesapeake City, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Chesapeake City has to offer?

HYDRANGEA HOUSE Waterview cozy 3-bdrm Getaway in quiet Chesapeake City AC & yard: This highly rated holiday home rental in Chesapeake City 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 that you can cook with friends or family. Other favourite homes for rent in Chesapeake City are Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun! and Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows .

How many holiday rentals are there in Chesapeake City?

With 10 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Chesapeake City?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesapeake City. Holiday rentals offer extras such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from public hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family trip.