Book Holiday Homes in Chesapeake City

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Featured Holiday Homes in Chesapeake City

Chesapeake Bay House with Dock & Private Beach

Chesapeake Bay House with Dock & Private Beach

Elkton
Located in Elkton, this vacation home is on the waterfront, within a 15-minute drive of Chesland Park and Chesapeake City Bridge.
Opens in a new windowChesapeake Bay House with Dock & Private Beach
Waterfront house with amazing views. Top of the Chesapeake

Waterfront house with amazing views. Top of the Chesapeake

Perryville
Located in Perryville, this vacation home is on the waterfront, within a 5-minute drive of Chestnut Point Estates and Marina and Craft Haven Marina.
Opens in a new windowWaterfront house with amazing views. Top of the Chesapeake
Nancy’s Touch, A Waterfront Paradise!

Nancy’s Touch, A Waterfront Paradise!

North East
Located in North East, this vacation home is on the waterfront, within a 10-minute drive of Roachs Shore and Elk Neck State Park.
Opens in a new windowNancy’s Touch, A Waterfront Paradise!
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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.
Opens in a new windowBeachfront Sunsets on the Water at Oakwood Beach
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!!!

Chesapeake City
A stay at this vacation home places you in the heart of Chesapeake City, steps from Chesapeake City Bridge and South Chesapeake City Historic District.
Opens in a new windowHook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
Waterfront Home,Private Dock,Bring Boat,Eastern shore, Betterton,Chestertown

Waterfront Home,Private Dock,Bring Boat,Eastern shore, Betterton,Chestertown

Worton
Located in Worton, this vacation home is on the waterfront, within a 15-minute drive of Betterton Community Park and Betterton Historic District.
Opens in a new windowWaterfront Home,Private Dock,Bring Boat,Eastern shore, Betterton,Chestertown
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

Newark
The price is AU$513 per night from 2 Nov to 3 Nov
AU$513
2 Nov - 3 Nov
includes taxes & fees
With a stay at this vacation home in Newark, you'll be within a 10-minute drive of Christiana Mall and University of Delaware.
Opens in a new windowSerene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Charming 3-bedroom house with WiFi, AC in Newark DE, walking distance to UDEL

Charming 3-bedroom house with WiFi, AC in Newark DE, walking distance to UDEL

Newark
Located in Newark, this vacation home is within a 15-minute drive of University of Delaware and Christiana Mall.
Opens in a new windowCharming 3-bedroom house with WiFi, AC in Newark DE, walking distance to UDEL
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, a 3-minute drive from Wilmington Riverwalk and 12 minutes from Christiana ...
Opens in a new windowWilmington Comfort 4 Min to Riverfront fenced yard
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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
AU$90
Highest Price
AU$513
Popular accommodation
Chesapeake Bay House with Dock & Private Beach, Waterfront house with amazing views. Top of the Chesapeake, Nancy’s Touch, A Waterfront Paradise!, Beachfront Sunsets on the Water at Oakwood Beach, Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!, Waterfront Home,Private Dock,Bring Boat,Eastern shore, Betterton,Chestertown, Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE, Charming 3-bedroom house with WiFi, AC in Newark DE, walking distance to UDEL, Wilmington Comfort 4 Min to Riverfront fenced yard

Top trending hotels in Chesapeake City

Historic Chesapeake City Stay

Historic Chesapeake City Stay

Chesapeake City
The price is AU$430 per night from 2 Nov to 3 Nov
AU$430
2 Nov - 3 Nov
includes taxes & fees
Located in Chesapeake City, this cabin is on a river, a 2-minute walk from Chesapeake City Bridge and within a 5-minute drive of Cecil County Public Library ...
Opens in a new windowHistoric Chesapeake City Stay
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$198 per night from 2 Nov to 3 Nov
AU$198
2 Nov - 3 Nov
includes taxes & fees
When you stay at Sonesta Select Newark Christiana Mall in Newark, you'll be in the business district, a 4-minute drive from Christiana Mall and 10 minutes from ...
Opens in a new windowSonesta Select Newark Christiana Mall
Quality Inn Newark - Wilmington

Quality Inn Newark - Wilmington

2.5 out of 5
65 Geoffrey Dr, Newark, DE
Fully refundableReserve now, pay when you stay
The price is AU$90 per night from 21 Nov to 22 Nov
AU$90
21 Nov - 22 Nov
includes taxes & fees
With a stay at Quality Inn Newark - Wilmington in Newark, you'll be within a 15-minute drive of Christiana Mall and University of Delaware.
Opens in a new windowQuality Inn Newark - Wilmington
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Comfort Inn & Suites Newark - Wilmington

Comfort Inn & Suites Newark - Wilmington

2.5 out of 5
3 Concord Ln, Newark, DE
Fully refundableReserve now, pay when you stay
The price is AU$149 per night from 6 Nov to 7 Nov
AU$149
6 Nov - 7 Nov
includes taxes & fees
When you stay at Comfort Inn & Suites Newark - Wilmington in Newark, you'll be in the business district, a 4-minute drive from Christiana Mall and 7 minutes ...
Opens in a new windowComfort Inn & Suites Newark - Wilmington
Don't see what you're looking for?
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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.