Chesapeake City Vacation Rentals

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Vacation Rentals in Chesapeake City

5-bedroom vacation home 5 minutes from historic Charlestown

Perryville MD

$494 nightly

$524 total

Mar 11 - Mar 12

Total with taxes and 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.

Kitchen

Washer

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

Chesapeake City MD

With a stay at this vacation home in Chesapeake City, you'll be just steps from Ferryslip Road Park and Chesapeake City Town Hall.

Pool

Hot Tub

Elegant Family Stay • Quiet Neighborhood • Comfort

New Castle DE

$280 nightly

$291 total

Mar 25 - Mar 26

Total with taxes and fees

With a stay at this vacation home in New Castle, you'll be within a 15-minute drive of Christiana Mall and Dragon Run Park.

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

Wilmington DE

$124 nightly

$129 total

Mar 11 - Mar 12

Total with taxes and fees

With a stay at this vacation home in Wilmington (South Wilmington), you'll be within a 15-minute drive of Wilmington Riverwalk and Christiana Mall.

Kitchen

Washer

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Elkton MD

Located in Elkton, this vacation home is a 3-minute drive from Upper Bay Museum and 6 minutes from Milburn Stone Theater.

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 Betterton Beach.

Kitchen

Washer

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.

Hot Tub

Kitchen

Chesapeake Bay House with Dock & Private Beach

Elkton MD

Located in Elkton, this vacation home is on the waterfront, within a 15-minute drive of Chesland Park and Chesapeake City Bridge.

Kitchen

Washer

New Construction townhome close to everything downtown w/transparent pricing

Wilmington DE

With a stay at this vacation home in Wilmington (Hilltop), you'll be within a 15-minute drive of Wilmington Riverwalk and Christiana Mall.

Spring 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 South Chesapeake City Historic District.

Welcome to the secluded waterfront oasis

Millington MD

Located in Millington, this vacation home is on the waterfront, within a 10-minute drive of Crumpton Auction and Crumpton Park.

Nancy’s Touch, A Waterfront Paradise!

North East MD

Located in North East, this vacation home is on the waterfront, within a 10-minute drive of Roachs Shore and Elk Neck State Park.

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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.