Chesapeake City Holiday Rentals

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Check prices for these dates

Tonight
15 Oct - 16 Oct
Tomorrow
16 Oct - 17 Oct
This weekend
17 Oct - 19 Oct
Next weekend
24 Oct - 26 Oct

Holiday Rentals in Chesapeake City

Marina
Historic Chesapeake City Stay
Historic Chesapeake City Stay
9.0 out of 10, Wonderful, (15)
"Always a nice get away…."
The price is AU$432
includes taxes & fees
16 Oct - 17 Oct
Historic Chesapeake City Stay
Marina
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
9.8 out of 10, Exceptional, (6)
"We rented Hook, Wine & Sinker for our family to stay in during the weekend of our son's wedding in Chesapeake City, MD. The home is absolutely beautiful, very clean, spacious, and one of the best rentals that I've stayed in with VRBO. "
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
Exterior
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
10.0 out of 10, Exceptional, (56)
"Amazing weekend on the river with a fantastic house. "
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
Outdoor dining
Chesapeake Bay House with Dock & Private Beach
Chesapeake Bay House with Dock & Private Beach
10.0 out of 10, Exceptional, (174)
"Nice property. Large enough for 13. Plenty of space to spread out "
Chesapeake Bay House with Dock & Private Beach
Fridge, microwave, oven, stovetop
Charming 2-bedroom house with WiFi, AC in marvelous Wilmington
Charming 2-bedroom house with WiFi, AC in marvelous Wilmington
2.0 out of 10, (2)
"Never heard from host. Expedia had to cancel reservation."
The price is AU$194
includes taxes & fees
19 Oct - 20 Oct
Charming 2-bedroom house with WiFi, AC in marvelous Wilmington
Smart TV, books
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
10.0 out of 10, Exceptional, (25)
"Very nice cottage, as advertised"
The price is AU$323
includes taxes & fees
21 Oct - 22 Oct
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Terrace/patio
Waterfront house with amazing views. Top of the Chesapeake
Waterfront house with amazing views. Top of the Chesapeake
10.0 out of 10, Exceptional, (100)
"The river house has an absolutely amazing view! My kids were thrilled with the chance to fish off a very long dock and even get their feet in the water on a small beach below the house (when the tide was out). Overall, the house was perfect and just big enough for our large family of seven. Matt was very responsive to a few questions I had and was a wonderful host! "
Waterfront house with amazing views. Top of the Chesapeake
Smart TV, books
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (57)
"Lovely cottage, well-equipped, immaculately clean. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Property grounds
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
9.8 out of 10, Exceptional, (11)
"It was a lovely home and we very much enjoyed our stay. Clean, comfortable beds and great location. "
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Terrace/patio
Nancy’s Touch, A Waterfront Paradise!
Nancy’s Touch, A Waterfront Paradise!
10.0 out of 10, Exceptional, (171)
"The house was quaint, scenic, well maintained and in a great location with a breathtaking view of the bay. We had a wonderful time there, would definitely recommend it and would love to revisit again. "
Nancy’s Touch, A Waterfront Paradise!
On the beach, sun-loungers, beach towels
Beachfront Sunsets on the Water at Oakwood Beach
Beachfront Sunsets on the Water at Oakwood Beach
10.0 out of 10, Exceptional, (42)
"Stayed here for my daughter’s softball tournament. The house is adorable and had plenty of everything that we needed. "
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
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
9.8 out of 10, Exceptional, (50)
"This property was perfect for our trip. It was very clean, comfortable and feels like home. Description and photos on the website were accurate. The owners were very attentive and hospitable. This is definite a place I’ll return to."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Interior
Charming 2-bedroom cabin close to Fair Hill on horse farm
Charming 2-bedroom cabin close to Fair Hill on horse farm
9.6 out of 10, Exceptional, (8)
"Good experience"
Charming 2-bedroom cabin close to Fair Hill on horse farm
Spa
Stunning waterfront villa with indoor pool and kids swing set and play area.
Stunning waterfront villa with indoor pool and kids swing set and play area.
9.8 out of 10, Exceptional, (19)
"Wonderful location, lots to do, close to Chesapeake City, excellent host"
Stunning waterfront villa with indoor pool and kids swing set and play area.
Sun-loungers, beach towels
5-bedroom vacation home 5 minutes from historic Charlestown
5-bedroom vacation home 5 minutes from historic Charlestown
9.8 out of 10, Exceptional, (145)
"Nice property with amazing views. Celebrated college graduation with family. Young ones had fun looking at ducks. Plenty of room for a large group."
The price is AU$932
includes taxes & fees
20 Oct - 21 Oct
5-bedroom vacation home 5 minutes from historic Charlestown
Exterior
Waterfront Home,Private Dock,Bring Boat,Eastern shore, Betterton,Chestertown
Waterfront Home,Private Dock,Bring Boat,Eastern shore, Betterton,Chestertown
9.8 out of 10, Exceptional, (94)
"The properly is in great shape, clean and well provisioned. The flat back yard is perfect for yard games and when the tide is low, there a little private beach! The kids played in the sand and floated around Still Pound Creek all weekend. Loretta was an excellent host!"
Waterfront Home,Private Dock,Bring Boat,Eastern shore, Betterton,Chestertown
Interior
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
9.8 out of 10, Exceptional, (19)
"Clean and comfortable stay in quiet neighborhood! Communication with the host was pleasant and prompt."
The price is AU$517
includes taxes & fees
21 Oct - 22 Oct
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Beach
Waterfront Retreat with Private Dock and Beach
Waterfront Retreat with Private Dock and Beach
10.0 out of 10, Exceptional, (24)
"Quiet and relaxing spot right on the water"
The price is AU$486
includes taxes & fees
2 Nov - 3 Nov
Waterfront Retreat with Private Dock and Beach
Fridge, microwave, oven, stovetop
Tiny Home Tranquil Oasis
Tiny Home Tranquil Oasis
The price is AU$375
includes taxes & fees
16 Oct - 17 Oct
Tiny Home Tranquil Oasis
1 bedroom
Summer Rustic Camping with AC and King Bed
Summer Rustic Camping with AC and King Bed
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."
The price is AU$274
includes taxes & fees
4 Nov - 5 Nov
Summer Rustic Camping with AC and King Bed
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

Embassy Suites by Hilton Newark Wilmington South

Embassy Suites by Hilton Newark Wilmington South

10/10 Excellent
"Much nicer than I expected. It was parents weekend, so cost more than it should. "
Victoria 2-night trip
Posted 2 days ago
Embassy Suites by Hilton Newark Wilmington South

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$194 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 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 Bohemia Bay Yacht Harbour 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.