Book Holiday Homes in Chesapeake City

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Featured Holiday Homes in Chesapeake City

Tip Of The Town Fresh and New 3 Bedroom Nest

Tip Of The Town Fresh and New 3 Bedroom Nest

North East
Stay at this vacation home in North East. Enjoy free WiFi, a water park, and a garden. Popular attractions Upper Bay Museum and Milburn Stone Theater are located ...
Opens in a new windowTip Of The Town Fresh and New 3 Bedroom Nest
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

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

Havre De Grace
Book a stay at this family-friendly vacation home in Havre De Grace. Enjoy free WiFi, a water park, and a garden. Popular attractions Susquehanna Museum at the ...
Opens in a new windowCozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
Sailor's Sunrise Cottage - Chesapeake Bay

Sailor's Sunrise Cottage - Chesapeake Bay

Perryville
Stay at this vacation home in Perryville. Enjoy laundry facilities, an in-room coffeemaker, and in-room fireplaces. Popular attractions Craft Haven Marina and ...
Opens in a new windowSailor's Sunrise Cottage - Chesapeake Bay
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Charming 2-bedroom house with WiFi, AC in marvelous Wilmington

Charming 2-bedroom house with WiFi, AC in marvelous Wilmington

Wilmington
The price is NZ$212 per night from 22 Sept to 23 Sept
NZ$212
22 Sept - 23 Sept
includes taxes & fees
Stay at this vacation home in Wilmington. Enjoy a garden, laundry facilities, and air conditioning. Popular attractions Wilmington Riverwalk and Christina Park ...
Opens in a new windowCharming 2-bedroom house with WiFi, AC in marvelous Wilmington
Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!

Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!

Chesapeake City
Stay at this vacation home in Chesapeake City. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions South Chesapeake City Historic District ...
Opens in a new windowElegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!
Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

Middletown
Stay at this vacation home in Middletown. Enjoy laundry facilities, balconies, and air conditioning. Popular attractions Middletown Historic District and Appoquinimink ...
Opens in a new windowSpacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6
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 laundry facilities. Popular attractions Upper Bay Museum and Milburn ...
Opens in a new windowTrendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

Millington
Stay at this vacation home in Millington. Enjoy laundry facilities, patios, and an in-room coffeemaker. Popular attractions Crumpton Park and Crumpton Auction ...
Opens in a new windowLark's Nest on the Chester River. Spacious, waterfront home with private dock.
Chesapeake Point | Waterfront w/ HOT TUB + Beach!

Chesapeake Point | Waterfront w/ HOT TUB + Beach!

Elkton
Stay at this vacation home in Elkton. Enjoy laundry facilities, balconies, and an in-room coffeemaker. Popular attractions Elk Forest Wildlife Management Area ...
Opens in a new windowChesapeake Point | Waterfront w/ HOT TUB + 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
158 Holiday Homes
Lowest Price
NZ$126
Highest Price
NZ$465
Popular accommodation
Tip Of The Town Fresh and New 3 Bedroom Nest, Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!, Sailor's Sunrise Cottage - Chesapeake Bay, Charming 2-bedroom house with WiFi, AC in marvelous Wilmington, Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!, Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6, Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio, Lark's Nest on the Chester River. Spacious, waterfront home with private dock., Chesapeake Point | Waterfront w/ HOT TUB + Beach!

Top trending hotels in Chesapeake City

Historic Chesapeake City Stay

Historic Chesapeake City Stay

Chesapeake City
The price is NZ$465 per night from 30 Sept to 1 Oct
NZ$465
30 Sept - 1 Oct
includes taxes & fees
Stay at this cabin in Chesapeake City. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Chesapeake City Bridge and The Pell Gardens are ...
Opens in a new windowHistoric Chesapeake City Stay
Embassy Suites by Hilton Newark Wilmington South

Embassy Suites by Hilton Newark Wilmington South

3.5 out of 5
654 S College Ave, Newark, DE
Fully refundableReserve now, pay when you stay
The price is NZ$218 per night from 5 Oct to 6 Oct
NZ$218
5 Oct - 6 Oct
includes taxes & fees
Stay at this 3.5-star business-friendly hotel in Newark. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Opens in a new windowEmbassy Suites by Hilton Newark Wilmington South
Red Roof Inn & Suites Newark - University

Red Roof Inn & Suites Newark - University

2 out of 5
1119 S College Avenue, Newark, DE
Fully refundableReserve now, pay when you stay
The price is NZ$126 per night from 21 Sept to 22 Sept
NZ$126
21 Sept - 22 Sept
includes taxes & fees
Stay at this hotel in Newark. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the clean rooms in our reviews. Popular attractions ...
Opens in a new windowRed Roof Inn & Suites Newark - University
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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$191 per night from 25 Sept to 26 Sept
NZ$191
25 Sept - 26 Sept
includes taxes & fees
Stay at this 3-star hotel in Newark. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in ...
Opens in a new windowSonesta Select Newark Christiana Mall
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.

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^Subject to availability and chosen travel dates.