Chesapeake City Holiday Rentals from €450: Search Short-Term Rentals

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Holiday Rentals in Chesapeake City

"Property was clean and close to everything in Chesapeake City"

includes taxes & fees

27 Nov - 28 Nov

"This home was absolutely magnificent! Location and scenery were wonderful. Just so much to keep our attention and kept us in awe. This was a family trip with siblings and soooo many wonderful memories were made. We are older now and it means more than ever before. Thank you to our host Jane who kept in touch and was so very attentive. Most gracious. We are already talking about going back. Cannot say enough it thank you from the bottom of our hearts.♥️"

"The house is roomy and was clean and well stocked."

"Our group of 15 gathered here for a long weekend in July to attend a family event in the area. The house was WONDERFUL, STYLISH & SPACIOUS. And Chesapeake City itself was a surprise bonus… several gift shops, a cute ice cream shop, coffee & breakfast cafe, dinner restaurants - all within walking distance! Loved: everything about the house… proximity to the quaint town… plenty of hot water… awesome AC upstairs…Brad the owner answered emails very quickly… *minor* issues: the main floor AC...

"it being off season,very quiet. the people in the surrounding neighborhood were very friendly, we had a great time, ash and christine were awsome host. we will deffinately go back again!"

On the beach, sun-loungers, beach towels

"Cute, up-to-date house, peaceful location, beautiful views. Well supplied kitchen, including sharp knives! Excellent communication with owner – prompt and helpful. Fast internet. Could use more bathroom surface areas; a few more hooks to hang clothes and towels; and an additional umbrella or two outside for shade. My mom, sister, and I thoroughly enjoyed our stay."

"This house exceeded our expectations! From the pictures, we knew it would be beautiful, but once we got there it seemed so much bigger and brighter than what the pictures show. Its so light and airy and was perfect for what we came for. It was VERY clean, each bedroom came with towels and makeup wipes. You can tell the hosts put a lot of thought into this home. We went in the fall, but was still such a wonderful time walking along the quiet beach and having drinks on the patio. Would highly...

"Very quaint and cute cottage really enjoyed sleeping on the porch , The sound of the waves because it was windy was so soothing. I felt We were on a sailboat."

"The house is cute and clean small house perfect for 9. Comfortable clean linens were provided. Easy to get to. Close to food and easy to get to University of Delaware. Host was easy to get in touch with. The only thing was no TV at all but we enjoyed our time."

"We really enjoyed the property. The location was within walking distance to the downtown area providing many food and shopping options. We were in MD for a lacrosse tournament which was minutes away from the house. The house was recently renovated, clean and bright. We had more than enough space for our group of 8."

includes taxes & fees

2 Dec - 3 Dec

"Couple little things were annoying. Overall a place/property we love. This was our third visit and plan for another."

"Loved the preserved historic quality of the property. So tastefully furnished and lovely. Nice and quiet neighborhood. The exposed beams certainly let you know when someone was in the room over your head but so worth it for the character."

"Wonderful place to stay!"

Beach nearby, sun-loungers, beach towels

"This house had the most amazing views and was clean and tidy. It was perfect for us and the dogs. The yard was clean and mowed and provided plenty of room for frisbee play which is part of my german shepherd's job. The kitchen was very adequate for our needs! As expected, the upstairs bedrooms were "historic" and the staircase was steep also "historic". The showers were perfect. We had a great visit and would love to come back here!"

"We enjoyed our stay. Condo was comfortable and very clean. It provided convenient access for our weekend plans in Kennedyville and Chestertown."

"Great value, was a great jumping point for our group, who was here for a wedding"

"Decided to try something different, and luckily found the Dockside Doghouse. Very comfortable, incredibly relaxing."

"Porch is filled with cobwebs. Steps inside need a lot of improvement. Inside was very clean, if dated. However I was pleased with the updated shower, refrigerator, kitchen. No tv made the down time lonely. Netflix did not work, nor did dvd player. For me I needed a much more closer bathroom on the second floor. Getting up 3 times a night to use bathroom & navigating those poorly constructed stairs was scary. I did not want to stay in the single bed right by front door. SUZANNE was very...

"Great!"

"The coziest house we have ever stayed at ! The host went above and beyond to have everything we could need! Would definitely recommend ! "

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Other types of properties in Chesapeake City you may be interested in

"Great people "

includes taxes & fees

2 Dec - 3 Dec

Desk, blackout curtains, iron/ironing board, free WiFi

"I especially liked the complementary breakfast which offered many choices. I liked that you could get coffee anytime. And fresh lemon infused water was available in the lobby. I also appreciated having a microwave, refrigerator and coffeemaker in my room. Extra pillows on the very comfortable bed were a plus, as was the controllable A/C thermostat. The effective blackout curtains & the quiet were wonderful! All in all, a very favorable experience."

includes taxes & fees

22 Dec - 23 Dec

"It was just ok"

includes taxes & fees

3 Dec - 4 Dec

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 €450 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.

Recent reviews of Chesapeake City properties

5/5 Excellent

"Great location, wonderful staff, clean quiet rooms "

A verified traveller stayed at Hyatt Place Wilmington Riverfront

Posted 2 days ago

Fairfield Inn & Suites Wilmington New Castle

5/5 Excellent

Well above average

"Clean, comfortable rooms though right off the interstate so a little noisy from the traffic. The breakfast was better than every other hotel we stayed in as it included fresh fruit. Reasonably priced. We would stay here again. "

A verified traveller stayed at Fairfield Inn & Suites Wilmington New Castle

Posted 3 days ago

Comfort Inn & Suites Newark - Wilmington

5/5 Excellent

"I especially liked the complementary breakfast which offered many choices. I liked that you could get coffee anytime. And fresh lemon infused water was available in the lobby. I also appreciated having a microwave, refrigerator and coffeemaker in my room. Extra pillows on the very comfortable bed were a plus, as was the controllable A/C thermostat. The effective blackout curtains & the quiet were wonderful! All in all, a very favorable experience."

A verified traveller stayed at Comfort Inn & Suites Newark - Wilmington

Posted 6 days ago

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 9 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?

Explore the area and cultural attractions such as C and D Canal Museum, or visit one of the family-friendly sights such as Frightland. Bohemia Vista Marina and Lums Pond State Park are a couple of places you'll find in the wider area.

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.

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Holiday Rentals in Chesapeake City

Check Chesapeake City holiday rental availability

Holiday Rentals in Chesapeake City

Historic Chesapeake City Stay

Chesapeake City Quiet Overlook

Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Waterfront house with amazing views. Top of the Chesapeake

Beachfront Sunsets on the Water at Oakwood Beach

Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Historic home in the heart of Main Street- walkable to shops and restaurants

Stunning waterfront villa with indoor pool and kids swing set and play area.

Beautiful Colonial Style Home in Nottingham PA

Amazing Waterfront Home on the Bush River

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

BEACH WITHOUT THE BUSTLE

Wilmington Comfort 4 Min to Riverfront fenced yard

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

A cottage on the shore of the Delaware River

Other types of properties in Chesapeake City you may be interested in

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Quality Inn

Find out more about Chesapeake City

Recent reviews of Chesapeake City properties

Hyatt Place Wilmington Riverfront

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Sonesta Select Newark Christiana Mall

Fairfield Inn & Suites Wilmington New Castle

Comfort Inn & Suites Newark - Wilmington

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Hilton Wilmington/Christiana

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Frequently asked questions