Book Holiday Homes in Chesapeake City

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Featured Holiday Homes in Chesapeake City

Baseball Lovers Paradise!

Baseball Lovers Paradise!

Aberdeen
Located in Aberdeen, this vacation home is within a 5-minute drive of Cal Ripken Museum and Ripken Stadium.
Baseball Lovers Paradise!
Beautiful Brick-Wall House in Historic Newcastle

Beautiful Brick-Wall House in Historic Newcastle

New Castle
With a stay at this vacation home in New Castle, you'll be within a 10-minute drive of Wilmington Riverwalk and Brandywine Valley.
Beautiful Brick-Wall House in Historic Newcastle
New Construction townhome close to everything downtown w/transparent pricing

New Construction townhome close to everything downtown w/transparent pricing

Wilmington
The price is AU$300 per night from 27 Jan to 28 Jan
AU$300
includes taxes & fees
27 Jan - 28 Jan
With a stay at this vacation home in Wilmington, you'll be within a 5-minute drive of Wilmington Riverwalk and Brandywine Valley.
New Construction townhome close to everything downtown w/transparent pricing
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Luxurious and spacious townhome with all necessary amenities awaits your stay.

Luxurious and spacious townhome with all necessary amenities awaits your stay.

Middletown
Located in Middletown, this vacation home is within a 5-minute drive of Middletown Historic District and The Everett Annex.
Luxurious and spacious townhome with all necessary amenities awaits your stay.
Beachfront Sunsets on the Water at Oakwood Beach

Beachfront Sunsets on the Water at Oakwood Beach

Salem
When you stay at this vacation home in Salem, you'll be on the beach, within a 5-minute drive of Delaware River and Salem River Wildlife Management Area.
Beachfront Sunsets on the Water at Oakwood Beach
Wilmington Comfort 4 Min to Riverfront fenced yard

Wilmington Comfort 4 Min to Riverfront fenced yard

Wilmington
With a stay at this vacation home, you'll be centrally located in Wilmington, within a 5-minute drive of Wilmington Riverwalk and Brandywine Valley.
Wilmington Comfort 4 Min to Riverfront fenced yard
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..

Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..

New Castle
With a stay at this vacation home in New Castle, you'll be on a river, within a 15-minute drive of Wilmington Riverwalk and Kirkwood Soccer Complex.
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
Spacious North East Home w/ Fenced Yard & Fire Pit

Spacious North East Home w/ Fenced Yard & Fire Pit

North East
Located in North East, this vacation home is a 1-minute drive from Upper Bay Museum and 6 minutes from Milburn Stone Theater.
Spacious North East Home w/ Fenced Yard & Fire Pit
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

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

Betterton
With a stay at this vacation home in Betterton, you'll be on the waterfront, just a 4-minute walk from Betterton Historic District and 7 minutes by foot from ...
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
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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.

Chesapeake City Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Chesapeake City vacation homes are the perfect way for you to wing it.

Holiday houses in Chesapeake City let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Chesapeake City in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Chesapeake City adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chesapeake City with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Chesapeake City vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Chesapeake City Holiday Homes essential information

Accommodation
113 Holiday Homes
Lowest Price
AU$95
Highest Price
AU$300
Popular accommodation
Baseball Lovers Paradise!, Beautiful Brick-Wall House in Historic Newcastle, New Construction townhome close to everything downtown w/transparent pricing , Luxurious and spacious townhome with all necessary amenities awaits your stay., Beachfront Sunsets on the Water at Oakwood Beach, Wilmington Comfort 4 Min to Riverfront fenced yard, Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping.., Spacious North East Home w/ Fenced Yard & Fire Pit, Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Top trending hotels in Chesapeake City

Quality Inn

Quality Inn

2.5 out of 5
65 Geoffrey Dr, Newark, DE
Fully refundableReserve now, pay when you stay
The price is AU$95 per night from 2 Feb to 3 Feb
AU$95
includes taxes & fees
2 Feb - 3 Feb
With a stay at Quality Inn in Newark, you'll be within a 15-minute drive of University of Delaware and Wilmington Riverwalk.
Quality Inn
Hilton Wilmington/Christiana

Hilton Wilmington/Christiana

4 out of 5
100 Continental Dr, Newark, DE
Fully refundableReserve now, pay when you stay
The price is AU$235 per night from 26 Jan to 27 Jan
AU$235
includes taxes & fees
26 Jan - 27 Jan
When you stay at Hilton Wilmington/Christiana in Newark, you'll be near the airport, within a 15-minute drive of University of Delaware and Wilmington ...
Hilton Wilmington/Christiana
Sonesta Select Newark Christiana Mall

Sonesta Select Newark Christiana Mall

3 out of 5
48 Geoffrey Dr, Newark, DE
Fully refundableReserve now, pay when you stay
The price is AU$177 per night from 20 Jan to 21 Jan
AU$177
includes taxes & fees
20 Jan - 21 Jan
When you stay at Sonesta Select Newark Christiana Mall in Newark, you'll be in the business district, within a 15-minute drive of University of Delaware and ...
Sonesta Select Newark Christiana Mall
Save an average of 15% on thousands of hotels when you're signed in
Red Roof Inn PLUS+ Wilmington - Newark

Red Roof Inn PLUS+ Wilmington - Newark

2.5 out of 5
415 Stanton Christiana Road, Newark, DE
Fully refundableReserve now, pay when you stay
The price is AU$127 per night from 22 Jan to 23 Jan
AU$127
includes taxes & fees
22 Jan - 23 Jan
When you stay at Red Roof Inn PLUS+ Wilmington - Newark in Newark, you'll be near the airport, within a 15-minute drive of University of Delaware and Wilmington ...
Red Roof Inn PLUS+ Wilmington - Newark
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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.

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^Subject to availability and chosen travel dates.