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)
"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.
The price is AU$420
includes taxes & fees
16 Jan - 17 Jan
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$505
includes taxes & fees
16 Jan - 17 Jan
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
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$245
includes taxes & fees
21 Jan - 22 Jan
Summer Rustic Camping with AC and King Bed
9.6 out of 10, Exceptional, (19 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is AU$190
includes taxes & fees
22 Jan - 23 Jan
Guest Suite for up to 2 in a Victorian on the Chester River
9.8 out of 10, Exceptional, (40 reviews)
"Absolutely love the accommodations. First impression when entering room was so fresh and clean."
United States
Beverly M.
The price is AU$170
includes taxes & fees
26 Jan - 27 Jan
Country Get Away 1 Bedroom Apartment
9.8 out of 10, Exceptional, (8 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is AU$244
includes taxes & fees
21 Jan - 22 Jan
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

Apartment in Bear

Cozy loft above ink shop
9.8 out of 10, Exceptional, (7 reviews)
"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.
The price is AU$177
includes taxes & fees
25 Jan - 26 Jan
Cozy loft above ink shop
10.0 out of 10, Exceptional, (11 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is AU$334
includes taxes & fees
21 Jan - 22 Jan
Quarry Landing - Center of Town & River View - 3 Bedroom
10.0 out of 10, Exceptional, (17 reviews)
"Grat time"
United States
Wanda B.
The price is AU$658
includes taxes & fees
21 Jan - 22 Jan
Thunder Hill Retreat - Spacious/Deck/Hot tub
9.6 out of 10, Exceptional, (23 reviews)
"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.
The price is AU$266
includes taxes & fees
25 Jan - 26 Jan
New Construction townhome close to everything downtown w/transparent pricing
10.0 out of 10, Exceptional, (2 reviews)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is AU$515
includes taxes & fees
16 Jan - 17 Jan
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
8.6 out of 10, Excellent, (14 reviews)
"Nice and quiet place to stay"
United States
Gary M.
The price is AU$425
includes taxes & fees
18 Jan - 19 Jan
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Holiday Home in Wilmington

A Cool Place to Stay in Wilmington DE
The price is AU$235
includes taxes & fees
18 Jan - 19 Jan
A Cool Place to Stay in Wilmington DE
The price is AU$215
includes taxes & fees
1 Feb - 2 Feb
Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
2.0 star property
The price is AU$946
includes taxes & fees
29 Jan - 30 Jan
Heated Pool • Private Backyard • Home Theater
10.0 out of 10, Exceptional, (34 reviews)
"Very secluded quaint cottage. Lovely space. Great overnight getaway. Port Deposit was just a few minutes drive. Will definitely stay again! "
United States
Tim R.
The price is AU$317
includes taxes & fees
19 Jan - 20 Jan
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Holiday Home in Kent County

High Tide Haven Suite
The price is AU$305
includes taxes & fees
25 Jan - 26 Jan
High Tide Haven Suite
The price is AU$618
includes taxes & fees
17 Jan - 18 Jan
Grandma’s Cottage will wrap around you like a warm hug
2.0 star property
The price is AU$304
includes taxes & fees
19 Jan - 20 Jan
Amish Countryside Escape at Forest Edge Farm
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$520
includes taxes & fees
21 Jan - 22 Jan
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$149 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?

Fall Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal: This highly rated holiday home rental in Chesapeake City offers a furnished patio, a garden and a BBQ to help you feel perfectly comfortable 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. Make the most of games in this rental home to help you unwind. Another good choice for your trip to Chesapeake City is Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!.

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 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.