Chesapeake City Holiday Rentals

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Our top choices for Chesapeake City holiday rentals

Cabin in Chesapeake City

Historic Chesapeake City Stay
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$393
includes taxes & fees
4 Mar - 5 Mar
Historic Chesapeake City Stay
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
The price is AU$434
includes taxes & fees
4 Mar - 5 Mar
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
9.8 out of 10, Exceptional, (40 reviews)
"Perfect in every way… a great stay"
United States
Robert B.
The price is AU$159
includes taxes & fees
9 Mar - 10 Mar
Country Get Away 1 Bedroom Apartment
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.
The price is AU$204
includes taxes & fees
4 Mar - 5 Mar
Summer Rustic Camping with AC and King Bed
10.0 out of 10, Exceptional, (38 reviews)
"Very cool place. "
United States
Eric L.
The price is AU$297
includes taxes & fees
5 Mar - 6 Mar
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
The price is AU$253
includes taxes & fees
11 Mar - 12 Mar
Amish Countryside Escape at Forest Edge Farm
8.0 out of 10, Very good, (12 reviews)
"Pleasant stay"
United States
Yommali G.
The price is AU$133
includes taxes & fees
15 Mar - 16 Mar
Charming 2-bedroom house in Aberdeen with WiFi and AC
10.0 out of 10, Exceptional, (11 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is AU$303
includes taxes & fees
9 Mar - 10 Mar
Quarry Landing - Center of Town & River View - 3 Bedroom
10.0 out of 10, Exceptional, (5 reviews)
"Loved the property and the decor. Very well done and luxurious!"
United States
Elisheva K.
The price is AU$677
includes taxes & fees
8 Mar - 9 Mar
Long Beach Cottage, (romantic couple’s getaway)
9.8 out of 10, Exceptional, (8 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is AU$229
includes taxes & fees
4 Mar - 5 Mar
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
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$455
includes taxes & fees
11 Mar - 12 Mar
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
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$271
includes taxes & fees
4 Mar - 5 Mar
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
8.6 out of 10, Excellent, (14 reviews)
"Great hole for our family to visit local family and celebrate Thanksgiving. Beds were comfortable house was clean and there were even Christmas lights and a tree up. So sweet. We enjoyed the fire pit and just hanging out. "
United States
Tiffany T.
The price is AU$399
includes taxes & fees
8 Mar - 9 Mar
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
10.0 out of 10, Exceptional, (19 reviews)
"Had a nice stay."
United States
Todd H.
The price is AU$617
includes taxes & fees
4 Mar - 5 Mar
Thunder Hill Retreat - Spacious/Deck/Hot tub
10.0 out of 10, Exceptional, (25 reviews)
"The apartment, including kitchen and bathroom, was very clean. Plenty of linens available for use. Perfect spot for fishing off of their dock. Very pleased with our reservation. "
United States
Debbie S.
The price is AU$440
includes taxes & fees
4 Mar - 5 Mar
Waterfront Retreat with Private Dock and Beach

Apartment in Bear

Cozy loft above ink shop
9.8 out of 10, Exceptional, (7 reviews)
"Second time staying in as many weeks. Place is spot on for what we needed for our quick trips. Close to food and shopping as well as easy access to highways if needed."
United States
Jeffrey R.
The price is AU$174
includes taxes & fees
7 Mar - 8 Mar
Cozy loft above ink shop
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$179
includes taxes & fees
24 Mar - 25 Mar
Guest Suite for up to 2 in a Victorian on the Chester River
9.6 out of 10, Exceptional, (23 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$249
includes taxes & fees
4 Mar - 5 Mar
New Construction townhome close to everything downtown w/transparent pricing
9.8 out of 10, Exceptional, (148 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$739
includes taxes & fees
4 Mar - 5 Mar
5-bedroom vacation home 5 minutes from historic Charlestown
9.2 out of 10, Wonderful, (9 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$496
includes taxes & fees
4 Mar - 5 Mar
Amazing Modern house with a full kitchen and parking
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$178 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?

Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows : This highly rated holiday home rental in Chesapeake City is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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.