Holiday Rentals in Chesapeake City

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Our top choices for Chesapeake City holiday rentals

Cabin in Chesapeake City

Historic Chesapeake City Stay
9.0 out of 10, Wonderful, (20)
"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 €244
includes taxes & fees
7 Jan - 8 Jan
Historic Chesapeake City Stay
9.4 out of 10, Exceptional, (3)
"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 €293
includes taxes & fees
10 Jan - 11 Jan
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
9.8 out of 10, Exceptional, (40)
"Absolutely love the accommodations. First impression when entering room was so fresh and clean."
United States
Beverly M.
The price is €99
includes taxes & fees
13 Jan - 14 Jan
Country Get Away 1 Bedroom Apartment
9.6 out of 10, Exceptional, (23)
"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 €143
includes taxes & fees
7 Jan - 8 Jan
New Construction townhome close to everything downtown w/transparent pricing

Apartment in Bear

Cozy loft above ink shop
9.8 out of 10, Exceptional, (6)
"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 €103
includes taxes & fees
7 Jan - 8 Jan
Cozy loft above ink shop
9.8 out of 10, Exceptional, (8)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is €141
includes taxes & fees
7 Jan - 8 Jan
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
9.6 out of 10, Exceptional, (19)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is €111
includes taxes & fees
13 Jan - 14 Jan
Guest Suite for up to 2 in a Victorian on the Chester River
9.6 out of 10, Exceptional, (5)
"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 €131
includes taxes & fees
7 Jan - 8 Jan
Summer Rustic Camping with AC and King Bed
10.0 out of 10, Exceptional, (29)
"Perfect location for that town. "
United States
Hisham M.
The price is €227
includes taxes & fees
7 Jan - 8 Jan
Private 3 room Queen Suite w/Kitchenette
9.6 out of 10, Exceptional, (5)
"Enjoyed our stay."
United States
Erik H.
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
10.0 out of 10, Exceptional, (17)
"Grat time"
United States
Wanda B.
Thunder Hill Retreat - Spacious/Deck/Hot tub
10.0 out of 10, Exceptional, (2)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is €308
includes taxes & fees
1 Feb - 2 Feb
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Holiday Home in Wilmington

A Cool Place to Stay in Wilmington DE
The price is €136
includes taxes & fees
7 Jan - 8 Jan
A Cool Place to Stay in Wilmington DE
10.0 out of 10, Exceptional, (34)
"What a cozy place to stay! The best part was in the morning when you can see the beautiful morning sky from the bed in the loft, the sun eloquently shining in through the windows and the deer frolicking in the yard. Comfy beds and plenty of lighting, would love to stay again."
United States
Bobbijo B.
The price is €184
includes taxes & fees
15 Jan - 16 Jan
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Free Breakfast. Pool. 10 Min Drive to the University of Delaware!
10.0 out of 10, Exceptional, (16)
"This is a lovely place, and we had a wonderful time. "
United States
Jonathan L.
Time for a re-set at this Farmette in the heart of southern Chester county!
10.0 out of 10, Exceptional, (1)
"We had a nice stay at this gorgeous house! Very comfortable and nicely appointed."
United States
Jordan K.
The price is €1,030
includes taxes & fees
20 Jan - 21 Jan
Spacious 4-bedroom house with backyard oasis

Holiday Home in Smyrna

JVA LUXURY HOUSING
10.0 out of 10, Exceptional, (1)
"The house was clean and wonderful. I highly recommend!"
United States
Daryl C.
The price is €517
includes taxes & fees
13 Jan - 14 Jan
JVA LUXURY HOUSING
8.6 out of 10, Excellent, (14)
"Nice and quiet place to stay"
United States
Gary M.
The price is €246
includes taxes & fees
7 Jan - 8 Jan
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
10.0 out of 10, Exceptional, (4)
"Loved the property and the decor. Very well done and luxurious!"
United States
Elisheva K.
The price is €352
includes taxes & fees
7 Jan - 8 Jan
Long Beach Cottage, (romantic couple’s getaway)
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.
Save an average of 15% on thousands of hotels when you're signed in

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, apart-hotels, 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 favorite 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 depends 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 €110 per night. Entering your travel dates in the search wizard you might find 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?

Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!: This highly rated holiday home rental in Chesapeake City is located on a river, and has a patio, an arcade/games room and air conditioning to put you at ease in your new surroundings. It has 5 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 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.