Book Holiday Homes in Chesapeake City

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Featured Holiday Homes in Chesapeake City

Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront

Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront

Perryville MD
When you stay at this vacation home in Perryville, you'll be on the waterfront, just steps from Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new windowUpper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront
Beachfront Sunsets on the Water at Oakwood Beach

Beachfront Sunsets on the Water at Oakwood Beach

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

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

Wilmington DE
The price is AU$179 per night from 16 Feb to 17 Feb
AU$179
16 Feb - 17 Feb
includes taxes & fees
With a stay at this vacation home in Wilmington (South Wilmington), you'll be within a 5-minute drive of Wilmington Riverwalk and Brandywine Valley.
Opens in a new windowCharming 2-bedroom house with WiFi, AC in marvelous Wilmington
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*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

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

Perryville MD
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 Chesapeake ...
Opens in a new window*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
Summer Season in Chesapeake City, MD  'Old Lock View'  @ C&D Canal

Summer Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal

Chesapeake City MD
With a stay at this vacation home in Chesapeake City, you'll be within a 5-minute drive of Chesapeake City Bridge and Brantwood Park.
Opens in a new windowSummer Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal
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
Luxury Waterfront Home Built for Entertaining!

Luxury Waterfront Home Built for Entertaining!

Abingdon MD
The price is AU$1,281 per night from 16 Feb to 17 Feb
AU$1,281
16 Feb - 17 Feb
includes taxes & fees
Located in Abingdon, this vacation home is within a 10-minute drive of Belcamp Beach and Queen Alexandra Hospital Online.
Opens in a new windowLuxury Waterfront Home Built for Entertaining!
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Elkton MD
The price is AU$401 per night from 16 Feb to 17 Feb
AU$401
16 Feb - 17 Feb
includes taxes & fees
With a stay at this vacation home in Elkton, you'll be within a 15-minute drive of Upper Bay Museum and Elk Neck State Park.
Opens in a new windowCharming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Modern cozy get-away* game room-amish country

Modern cozy get-away* game room-amish country

North East MD
Located in North East, this vacation home is a 4-minute drive from Milburn Stone Theater and 5 minutes from Calvert Regional Park.
Opens in a new windowModern cozy get-away* game room-amish country
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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
161 Holiday Homes
Lowest Price
AU$95
Highest Price
AU$1,281
Popular accommodation
Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront, Beachfront Sunsets on the Water at Oakwood Beach, Charming 2-bedroom house with WiFi, AC in marvelous Wilmington, *** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay, Summer Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal, Chesapeake Bay House with Dock & Private Beach, Luxury Waterfront Home Built for Entertaining!, Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck, Modern cozy get-away* game room-amish country

Top trending hotels in Chesapeake City

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$145 per night from 16 Feb to 17 Feb
AU$145
16 Feb - 17 Feb
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 University of Delaware and ...
Opens in a new windowSonesta Select Newark Christiana Mall
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 AU$160 per night from 22 Feb to 23 Feb
AU$160
22 Feb - 23 Feb
includes taxes & fees
When you stay at Embassy Suites by Hilton Newark Wilmington South in Newark, you'll be near the airport, just steps from Bob Carpenter Center and 9 minutes by ...
Opens in a new windowEmbassy Suites by Hilton Newark Wilmington South
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$95 per night from 28 Feb to 1 Mar
AU$95
28 Feb - 1 Mar
includes taxes & fees
With a stay at Quality Inn Newark - Wilmington in Newark, you'll be within a 15-minute drive of University of Delaware and Wilmington Riverwalk.
Opens in a new windowQuality Inn Newark - Wilmington
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Great Wolf Lodge Perryville

Great Wolf Lodge Perryville

2 out of 5
1240 Chesapeke Overlook Parkway Perryville MD
Fully refundable
The price is AU$315 per night from 18 Feb to 19 Feb
AU$315
18 Feb - 19 Feb
includes taxes & fees
With a stay at Great Wolf Lodge Perryville in Perryville, you'll be within a 15-minute drive of Ripken Stadium and Hollywood Casino.
Opens in a new windowGreat Wolf Lodge Perryville
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.