Chesapeake City Holiday Rentals

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Holiday Rentals in Chesapeake City

Pool
Historic Chesapeake City Stay
8.0 out of 10, Very good, (1)
"The place overall is very simple and nice. The bed was a little uncomfortable And decided to not stay the extra night and come home and use my own bed. Overall, very clean very nice."
The price is AU$357
includes taxes & fees
14 May - 15 May
Historic Chesapeake City Stay
Exterior
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
10.0 out of 10, Exceptional, (49)
"Dennis’s property was everything we needed. We had plenty of room for our 14 people. The separate houses were nice to give the infants and their parents a place to retreat to. The older kids loved the great room with the juke box where they could look out for boats. The house was well stocked which made it perfect for preparing our Thanksgiving dinner! Thanks Dennis!!"
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
1 bedroom, WiFi, bed sheets
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Property grounds
Chesapeake City Overlook: Breathtaking View!
10.0 out of 10, Exceptional, (2)
"Two of my brothers and an old friend came down to the c&d canal trail for a long weekend and a lot of bicycle riding. This house was right on the trail. A great house with great views. We were also within walking distance of a very good seafood restaurant. It was a perfect weekend. As far as the house it had everything we needed. We wanted for nothing. When we arrived at the house there was chocolates and snacks waiting for us as well as beers and sodas in the fridge with a note to help...
Chesapeake City Overlook: Breathtaking View!
Smart TV
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
9.6 out of 10, Exceptional, (5)
"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...
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
1 bedroom, WiFi, bed sheets
Oaxaca, a private room with private entrance
10.0 out of 10, Exceptional, (6)
"I hope to stay again!"
The price is AU$177
includes taxes & fees
14 May - 15 May
Oaxaca, a private room with private entrance
Pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (50)
"Had an excellent time at this beautiful and secluded property on the Chester River. Although very private and a lot of outside space to roam, we were still very close to all that Chestertown has to offer. So, it was the best of both worlds. Plenty of amazing scenery and wildlife to enjoy around the property, and Beth is an excellent communicator. If you're a wine drinker, check out a number of close-by wineries like: Casa Carmen, Bu-De, Broken Spoke and Crow Vineyards. Would highly recommend...
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Beach nearby, sun-loungers
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (36)
"Waterview cottage is comfortable and very clean. The accommodations look new and we had good sleep. The kitchen has most of the necessary equipment for meal preparation. A baking sheet pan is needed. WiFi and Roku TV was excellent. The primary bedroom bed was so tall/high my wife could not get in or out of it. That necessitated sleeping in the 2 twins. Plus, one of the twins was missing the top mini mattress. The view is mostly of the neighborhood street, nearby homes and their roofs and a small...
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Property grounds
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
9.8 out of 10, Exceptional, (80)
"House was fine. Odd they did not provide sheets. Was difficult for folks who came from far away. But the house was lovely and we enjoyed our time there!!"
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
Fridge, microwave, oven, stovetop
Stunning Home Steps minutes from Cal Ripken Stadium!!!
Stunning Home Steps minutes from Cal Ripken Stadium!!!
Exterior
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
9.8 out of 10, Exceptional, (85)
"Such a comfortable place to stay! Fully stocked kitchen, big rooms with comfortable beds and linens. Everything is clean and the appliances are new. Sweet welcome gift of pastries and water. Quiet neighborhood. Easy to access and property host was very responsive."
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
Interior
Historic home in the heart of Main Street- walkable to shops and restaurants
10.0 out of 10, Exceptional, (7)
"Minutes from our job site. Thank you for your hospitality."
Historic home in the heart of Main Street- walkable to shops and restaurants
Property grounds
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
10.0 out of 10, Exceptional, (65)
"We had a great get-away for a few days with our friends. The cabin was in a quiet neighborhood with amazing views. We especially enjoyed using the fire pit while sitting in the comfortable Adirondack chairs overlooking the Chesapeake Bay. The owners were friendly and great to work with. Highly recommend!"
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
Property grounds
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
9.2 out of 10, Wonderful, (9)
"Clean, great location. Had a very relaxing weekend that was greatly needed. There was plenty of things to see and do in the beautiful town. Had a small problem but the host took care of it immediately. He was great. Thank you for a wonderful time."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Property grounds
Cozy home with fenced in yard-Pet Friendly. 2 block walk to historic downtown!
9.6 out of 10, Exceptional, (42)
"Suzanne's place was very comfortable and she supplied everything you'd need. It was fun cooking in her kitchen and I was also able to work remotely as well."
Cozy home with fenced in yard-Pet Friendly. 2 block walk to historic downtown!
Fridge, microwave, oven, stovetop
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
9.8 out of 10, Exceptional, (27)
"This location was perfect for our stay during a bass tournament on the upper bay. boa parking was great and very secure compared to hotels. SAhelly was very accomadating"
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Property grounds
Family-Friendly Cottage, Walk to the Beach!
10.0 out of 10, Exceptional, (13)
"The cottage exceeded our expectations. Everything is as pictured. The place is sparkling clean and stocked with everything you need and more. Communication was excellent. Loved the location and the private beach access was a real plus. Great location to use as home base and take day trips in the area."
Family-Friendly Cottage, Walk to the Beach!
Aerial view
Thunder Hill Retreat - Peaceful - sleeps 12
10.0 out of 10, Exceptional, (4)
"Fantastic property, one the the best hosts we have ever had. I would recommend this house and this host to anyone. Above and beyond, we appreciate everything our host did in order for us to enjoy our stay."
The price is AU$857
includes taxes & fees
20 May - 21 May
Thunder Hill Retreat - Peaceful - sleeps 12
View from property
Beachfront Sunsets on the Water at Oakwood Beach
10.0 out of 10, Exceptional, (19)
"The location was great for us because it was relatively close to Newark, DE and Philadelphia. Water views were great from so much of the house and owners had thought of every possible touch to make people feel at home. There were plenty of outlets, chargers, TVs, tables & chairs, hooks in bathrooms, nightlights, etc. The fridge was free of all sorts of open condiments that are probably supposed to be helpful for guests but that drive my husband crazy as they've taken up half the fridge in the...
Beachfront Sunsets on the Water at Oakwood Beach
Fridge, microwave, oven, stovetop
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
10.0 out of 10, Exceptional, (17)
"Betty Ann’s property was exactly as described. The personal touches of full ice trays, cooler, a well-stocked kitchen and welcome snacks really show the care and thought Betty Ann takes in her rental. The sunsets are even more gorgeous than described- and literally 20 steps away. We loved our stay so much, we booked our next stay while we were there :) Keep in mind you are above the owners garage, so you make hear their use of it at any time!"
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
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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.

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

Terrace/patio
Sonesta Select Newark Christiana Mall
3.0 star property
8.0 out of 10, Very good, (1009)
"The stay was nice and so was the rooms . In my kids room there was a yellow stain on the blankets , even tho I couldn’t get a hold of the front desk I had to walk down to get a new blanket. There were kids playing on my kids door and running all night !! It was the worst my kids was really scared ! Even when we reported it kids was still knocking on their door and running . Other then that the hotel was nice ."
The price is AU$184
includes taxes & fees
26 May - 27 May
Sonesta Select Newark Christiana Mall
Sundeck
Red Roof Inn & Suites Newark - University
2.0 star property
5.8 out of 10, (1009)
"I decided to go with a jacuzzi tub room for a little extra and I'm not disappointed I did. The place needs some major updates done, the jacuzzi in the room had 2 broken knobs but still worked lol. The bathroom sink, tub, EVERYTHING was PAINTED white. I know this seems like some negative things i just want you to be aware what you're getting into lol. Its a decent little place for a decent price. I actually enjoyed our stay."
The price is AU$121
includes taxes & fees
14 May - 15 May
Red Roof Inn & Suites Newark - University
Desk, blackout curtains, iron/ironing board, free WiFi
Comfort Inn & Suites Newark - Wilmington
2.5 star property
9.0 out of 10, Wonderful, (1005)
"Good"
The price is AU$181
includes taxes & fees
16 May - 17 May
Comfort Inn & Suites Newark - Wilmington
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.

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$177 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.

How many holiday rentals are there in Chesapeake City?

With 6 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 The Patriot Ice Center. 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.

Recent reviews of Chesapeake City properties
Expedia verified reviews

Hilton Wilmington/Christiana

Hilton Wilmington/Christiana

5/5 Excellent
"For an impromptu stay everything was better than expected. "
A verified traveller stayed at Hilton Wilmington/Christiana
Posted 2 days ago
Hilton Wilmington/Christiana