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.
Chesapeake Bay House with Dock & Private Beach
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
A stay at this vacation home places you in the heart of Havre De Grace, within a 15-minute walk of Susquehanna Museum at the Lock House and Susquehanna ...
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
Stay & Play at Our Beautiful Retreat

Stay & Play at Our Beautiful Retreat

Elkton
Located in Elkton, this vacation home is in a rural location, within a 15-minute drive of Milburn Stone Theater and Lower Chrome Serpentine Barrens.
Stay & Play at Our Beautiful Retreat
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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
Located in Millington, this vacation home is on the waterfront, within a 10-minute drive of Crumpton Auction and Crumpton Park.
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
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
With a stay at this vacation home in Middletown, you'll be within a 5-minute drive of Middletown Historic District and The Everett Annex.
Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6
Walk to Town & River: Charming Home in North East!

Walk to Town & River: Charming Home in North East!

North East
Located in North East, this vacation home is a 2-minute drive from Upper Bay Museum and 5 minutes from Milburn Stone Theater.
Walk to Town & River: Charming Home in North East!
Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.

Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.

Havre de Grace
The price is AU$2,085 per night from 13 Aug to 14 Aug
AU$2,085
13 Aug - 14 Aug
includes taxes & fees
Located in Havre De Grace, this vacation home is in a rural location, a 1-minute drive from Susquehanna State Park and 9 minutes from Hosanna School Museum.
Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.
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
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

Perryville
When you stay at this vacation home in Perryville, you'll be on the waterfront, within a 5-minute drive of Chestnut Point Estates and Marina and Craft Haven ...
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
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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
162 Holiday Homes
Lowest Price
AU$117
Highest Price
AU$2,085
Popular accommodation
Chesapeake Bay House with Dock & Private Beach, Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!, Stay & Play at Our Beautiful Retreat, Lark's Nest on the Chester River. Spacious, waterfront home with private dock., Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6, Walk to Town & River: Charming Home in North East!, Relax in the woods with your own private pool - 4 BR house that sleeps up to 12., Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach, *** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

Top trending hotels in Chesapeake City

Historic Chesapeake City Stay

Historic Chesapeake City Stay

Chesapeake City
The price is AU$432 per night from 24 Aug to 25 Aug
AU$432
24 Aug - 25 Aug
includes taxes & fees
With a stay at this cabin in Chesapeake City, you'll be a 2-minute walk from Chesapeake City Bridge and within a 5-minute drive of Cecil County Public Library ...
Historic 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$172 per night from 18 Aug to 19 Aug
AU$172
18 Aug - 19 Aug
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 ...
Sonesta Select Newark Christiana Mall
Extended Stay America Suites Newark Christiana Wilmington

Extended Stay America Suites Newark Christiana Wilmington

2.5 out of 5
333 Continental Dr, Newark, DE
Fully refundableReserve now, pay when you stay
The price is AU$132 per night from 17 Aug to 18 Aug
AU$132
17 Aug - 18 Aug
includes taxes & fees
With a stay at Extended Stay America Suites Newark Christiana Wilmington in Newark, you'll be a 4-minute drive from Christiana Mall and 10 minutes from University ...
Extended Stay America Suites Newark Christiana Wilmington
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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 AU$117 per night from 13 Aug to 14 Aug
AU$117
13 Aug - 14 Aug
includes taxes & fees
Located in Newark, Red Roof Inn & Suites Newark - University is in the business district, within a 5-minute drive of Bob Carpenter Center and University of ...
Red Roof Inn & Suites Newark - University
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.