Book Holiday Homes in Chesapeake City

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Featured Holiday Homes in Chesapeake City

Baseball Lovers Paradise!

Baseball Lovers Paradise!

Aberdeen
Stay at this vacation home in Aberdeen. Enjoy air conditioning. Popular attractions Ripken Stadium and Cal Ripken Museum are located nearby.
Baseball Lovers Paradise!
New Construction townhome close to everything downtown w/transparent pricing

New Construction townhome close to everything downtown w/transparent pricing

Wilmington
Stay at this vacation home in Wilmington. Enjoy an in-room coffeemaker, in-room fireplaces, and air conditioning. Popular attractions Wilmington Riverwalk and ...
New Construction townhome close to everything downtown w/transparent pricing
Cozy 5 bedroom house with attached guest suite

Cozy 5 bedroom house with attached guest suite

Worton
Stay at this vacation home in Worton. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Betterton Community Park and Betterton ...
Cozy 5 bedroom house with attached guest suite
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Beautiful Brick-Wall House in Historic Newcastle

Beautiful Brick-Wall House in Historic Newcastle

New Castle
Stay at this vacation home in New Castle. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Wilmington Riverwalk and Delaware ...
Beautiful Brick-Wall House in Historic Newcastle
Beachfront Sunsets on the Water at Oakwood Beach

Beachfront Sunsets on the Water at Oakwood Beach

Salem
Book a stay at this beach vacation home in Salem. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Hickory Island and Fort Delaware State Park ...
Beachfront Sunsets on the Water at Oakwood Beach
Beautiful Colonial Style Home in Nottingham PA

Beautiful Colonial Style Home in Nottingham PA

Nottingham
Stay at this vacation home in Nottingham. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Nottingham County Park and Nottingham Park ...
Beautiful Colonial Style Home in Nottingham PA
Spacious North East Home w/ Fenced Yard & Fire Pit

Spacious North East Home w/ Fenced Yard & Fire Pit

North East
Stay at this vacation home in North East. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Upper Bay Museum and Veterans Park are ...
Spacious North East Home w/ Fenced Yard & Fire Pit
Wilmington Comfort 4 Min to Riverfront fenced yard

Wilmington Comfort 4 Min to Riverfront fenced yard

Wilmington
Book a stay at this family-friendly vacation home in Wilmington. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions Wilmington Riverwalk ...
Wilmington Comfort 4 Min to Riverfront fenced yard
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Elkton
Book a stay at this family-friendly vacation home in Elkton. Enjoy free WiFi, a garden, and furnished patios. Popular attractions Upper Bay Museum and Milburn ...
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
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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
117 Holiday Homes
Lowest Price
NZ$141
Highest Price
NZ$467
Popular accommodation
Baseball Lovers Paradise!, New Construction townhome close to everything downtown w/transparent pricing , Cozy 5 bedroom house with attached guest suite, Beautiful Brick-Wall House in Historic Newcastle, Beachfront Sunsets on the Water at Oakwood Beach, Beautiful Colonial Style Home in Nottingham PA, Spacious North East Home w/ Fenced Yard & Fire Pit, Wilmington Comfort 4 Min to Riverfront fenced yard, Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Top trending hotels in Chesapeake City

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 NZ$141 per night from 2 Mar to 3 Mar
NZ$141
includes taxes & fees
2 Mar - 3 Mar
Stay at this hotel in Newark. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
Red Roof Inn PLUS+ Wilmington - Newark
Great Wolf Lodge Perryville

Great Wolf Lodge Perryville

2 out of 5
1240 Chesapeke Overlook Parkway, Perryville, MD
Fully refundableReserve now, pay when you stay
The price is NZ$467 per night from 26 Feb to 27 Feb
NZ$467
includes taxes & fees
26 Feb - 27 Feb
Stay at this hotel in Perryville. Enjoy free WiFi, 4 restaurants, and water park access (surcharge). Popular attractions Hollywood Casino and Garrett Island ...
Great Wolf Lodge Perryville
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 NZ$186 per night from 2 Mar to 3 Mar
NZ$186
includes taxes & fees
2 Mar - 3 Mar
Stay at this 3-star business-friendly hotel in Newark. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean ...
Sonesta Select Newark Christiana Mall
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Hyatt Place Wilmington Riverfront

Hyatt Place Wilmington Riverfront

3 out of 5
760 Justison Street, Wilmington, DE
Fully refundableReserve now, pay when you stay
The price is NZ$292 per night from 9 Mar to 10 Mar
NZ$292
includes taxes & fees
9 Mar - 10 Mar
Stay at this 3-star business-friendly hotel in Wilmington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
Hyatt Place Wilmington Riverfront
Don't see what you're looking for?
See all available properties in Chesapeake City
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.