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, (20 reviews)
"Cleaned, beautifully decorated, not like a rental but more like a home!"
United States
Manjetjola P.
The price is AU$391
includes taxes & fees
20 Apr - 21 Apr
Historic Chesapeake City Stay

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
10.0 out of 10, Exceptional, (40 reviews)
"Very unique and cozy property close to everything we needed. "
United States
John H.
The price is AU$295
includes taxes & fees
19 Apr - 20 Apr
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Long Beach Cottage, (romantic couple’s getaway)

Long Beach Cottage, (romantic couple’s getaway)
Charlestown
10.0 out of 10, Exceptional, (6 reviews)
"Nice, quaint house, right on the water. Perfect for couples looking to relax. "
United States
Mike F.
The price is AU$596
includes taxes & fees
21 Apr - 22 Apr
Long Beach Cottage, (romantic couple’s getaway)

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, (21 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$460
includes taxes & fees
22 Apr - 23 Apr
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

Nature's Haven Tiny Home

Nature's Haven Tiny Home
Bear
10.0 out of 10, Exceptional, (4 reviews)
"Nature’s Haven Tiny Home worked great for us. Karin was a great communicator and we really enjoyed ourselves. "
United States
James S.
The price is AU$328
includes taxes & fees
20 Apr - 21 Apr
Nature's Haven Tiny Home

Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (40 reviews)
"This place is out in the country, but a short distance to lots of places we wanted to see, shop at, visit."
United States
Richard
The price is AU$158
includes taxes & fees
29 Apr - 30 Apr
Country Get Away Studio Apartment

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)
"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.
The price is AU$219
includes taxes & fees
20 Apr - 21 Apr
Summer Rustic Camping with AC and King Bed

Quarry Landing - Center of Town & River View - 3 Bedroom

Quarry Landing - Center of Town & River View - 3 Bedroom
Port Deposit
10.0 out of 10, Exceptional, (11 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is AU$331
includes taxes & fees
22 Apr - 23 Apr
Quarry Landing - Center of Town & River View - 3 Bedroom

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
9.8 out of 10, Exceptional, (8 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is AU$227
includes taxes & fees
18 Apr - 19 Apr
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

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
9.6 out of 10, Exceptional, (20 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is AU$177
includes taxes & fees
29 Apr - 30 Apr
Guest Suite for up to 2 in a Victorian on the Chester River

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, (14 reviews)
"Met our needs. Great stay."
United States
Robert C.
The price is AU$132
includes taxes & fees
10 May - 11 May
Charming 2-bedroom house in Aberdeen with WiFi and AC

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, (5 reviews)
"It is a warm and welcoming little home away from home. We will be back!"
United States
Brittany C.
The price is AU$288
includes taxes & fees
21 Apr - 22 Apr
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

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

Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
Newark
The price is AU$246
includes taxes & fees
19 Apr - 20 Apr
Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!

Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm
Nottingham
10.0 out of 10, Exceptional, (1 review)
The price is AU$306
includes taxes & fees
22 Apr - 23 Apr
Amish Countryside Escape at Forest Edge Farm

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, (24 reviews)
"Property was spacious with open kitchen/living room area and 2 bedrooms with their own baths."
United States
Mark F.
The price is AU$389
includes taxes & fees
19 Apr - 20 Apr
New Construction townhome close to everything downtown w/transparent pricing

5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
9.8 out of 10, Exceptional, (151 reviews)
"Magical and made tons of family wedding memories. What a perfect house on the river!! We will be booking again"
United States
Mary D.
The price is AU$738
includes taxes & fees
20 Apr - 21 Apr
5-bedroom vacation home 5 minutes from historic Charlestown

Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
The price is AU$336
includes taxes & fees
20 Apr - 21 Apr
Tiny Home Tranquil Oasis

Amazing Modern house with a full kitchen and parking

Amazing Modern house with a full kitchen and parking
Smyrna
9.2 out of 10, Wonderful, (10 reviews)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
United States
Laurie S.
The price is AU$463
includes taxes & fees
5 May - 6 May
Amazing Modern house with a full kitchen and parking

High Tide Haven Suite

High Tide Haven Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"The suite was really nice and extremely clean. Comfy, memory foam bed. Excellent shower with great water pressure. The ambiance in the room is serene and beachy making for a wonderful escape. Absolutely loved their screened in porch and view from the back deck. The hosts were very nice, had great communication and served the most delicious bagels. We left our phone charger there and they promptly called us in time to turn around and get it. Highly recommend this location and will stay there...
United States
Joell V.
The price is AU$232
includes taxes & fees
20 Apr - 21 Apr
High Tide Haven Suite

Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (19 reviews)
"The house is very spacious with comfortable beds and numerous activities and games for the family. The hot tub was a feature we all truly enjoyed, especially while watching the snow come down.The location is very tranquil and the views are beautiful!The owner is very responsive to messages and was understanding when one of us had an issue requiring a later checkout. We would definitely book a future stay at Thunderhill!"
United States
Heather W.
The price is AU$721
includes taxes & fees
28 Apr - 29 Apr
Thunder Hill Retreat - Spacious/Deck/Hot tub
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$175 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?

Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!: This highly rated holiday home rental in Chesapeake City offers an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a patio, a garden and 1 hot tub so that you can immerse yourself in your holiday. Another good choice for your trip to Chesapeake City is Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows .

How many holiday rentals are there in Chesapeake City?

With 8 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 Chesapeake City Docks 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.