Book Holiday Homes in Chesapeake City

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Featured Holiday Homes in Chesapeake City

Sailor's Sunrise Cottage - Chesapeake Bay

Sailor's Sunrise Cottage - Chesapeake Bay

Perryville MD
When you stay at this vacation home in Perryville, you'll be on the waterfront, within a 10-minute walk of Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new windowSailor's Sunrise Cottage - Chesapeake Bay
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 MD
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 ...
Opens in a new windowHistoric Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Where luxury meets laughter by the bay.  Welcome to Bamboo Sands Villa & Captain’s Quarters.

Where luxury meets laughter by the bay. Welcome to Bamboo Sands Villa & Captain’s Quarters.

Worton MD
With a stay at this vacation home in Worton, you'll be on the waterfront, just steps from Still Pond Station Park and a 5-minute drive from Chesapeake Bay.
Opens in a new windowWhere luxury meets laughter by the bay. Welcome to Bamboo Sands Villa & Captain’s Quarters.
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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 DE
Located in Middletown, this vacation home is within a 5-minute drive of Middletown Historic District and The Everett Annex.
Opens in a new windowLuxurious and spacious townhome with all necessary amenities awaits your stay.
Sunset River Shack -amazing waterfront view

Sunset River Shack -amazing waterfront view

Elkton MD
Located in Elkton, this vacation home is on the waterfront, within a 10-minute drive of Chesland Park and Brantwood Park.
Opens in a new windowSunset River Shack -amazing waterfront view
Chesapeake Bay House with Dock & Private Beach

Chesapeake Bay House with Dock & Private Beach

Elkton MD
Located in Elkton, this vacation home is on the waterfront, within a 10-minute drive of Chesland Park and Brantwood Park.
Opens in a new windowChesapeake Bay House with Dock & Private Beach
5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown

Perryville MD
The price is AU$784 per night from 27 May to 28 May
AU$784
27 May - 28 May
includes taxes & fees
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 window5-bedroom vacation home 5 minutes from historic Charlestown
Beachfront Sunsets on the Water at Oakwood Beach

Beachfront Sunsets on the Water at Oakwood Beach

Salem NJ
Located in Salem, this vacation home is on the waterfront, a 4-minute drive from Salem River Wildlife Management Area and 10 minutes from Salem Medical ...
Opens in a new windowBeachfront Sunsets on the Water at Oakwood Beach
Cozy home w/fenced in yard-Dog Friendly with Pet fee. 2 block walk to downtown!

Cozy home w/fenced in yard-Dog Friendly with Pet fee. 2 block walk to downtown!

Havre De Grace MD
A stay at this vacation home places you in the heart of Havre De Grace, within a 15-minute walk of Lock House Museum and Susquehanna River.
Opens in a new windowCozy home w/fenced in yard-Dog Friendly with Pet fee. 2 block walk to downtown!
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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
150 Holiday Homes
Lowest Price
AU$105
Highest Price
AU$784
Popular accommodation
Sailor's Sunrise Cottage - Chesapeake Bay, Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach, Where luxury meets laughter by the bay. Welcome to Bamboo Sands Villa & Captain’s Quarters., Luxurious and spacious townhome with all necessary amenities awaits your stay., Sunset River Shack -amazing waterfront view, Chesapeake Bay House with Dock & Private Beach, 5-bedroom vacation home 5 minutes from historic Charlestown, Beachfront Sunsets on the Water at Oakwood Beach, Cozy home w/fenced in yard-Dog Friendly with Pet fee. 2 block walk to downtown!

Top trending hotels in Chesapeake City

Quality Inn Newark - Wilmington

Quality Inn Newark - Wilmington

2.5 out of 5
65 Geoffrey Dr Newark DE
Fully refundable
The price is AU$105 per night from 2 June to 3 June
AU$105
2 June - 3 June
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
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$144 per night from 28 May to 29 May
AU$144
28 May - 29 May
includes taxes & fees
When you stay at Sonesta Select Newark Christiana Mall in Newark, you'll be in the business district, within a 15-minute drive of Christiana Mall and University ...
Opens in a new windowSonesta Select Newark Christiana Mall
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$115 per night from 24 May to 25 May
AU$115
24 May - 25 May
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 ...
Opens in a new windowRed Roof Inn & Suites Newark - University
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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 AU$280 per night from 27 May to 28 May
AU$280
27 May - 28 May
includes taxes & fees
Located in Perryville, Great Wolf Lodge Perryville is a 1-minute drive from Hollywood Casino and 8 minutes from Garrett Island Beach.
Opens in a new windowGreat Wolf Lodge Perryville
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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.