Chesapeake City Vacation Rentals

Name: A Cool Place to Stay in Wilmington DE
Price range: $155 total

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Vacation Rentals in Chesapeake City

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

Perryville MD

When you a stay at this vacation home in Perryville, you'll be on the waterfront, just steps from Chesapeake Bay and Northern Chesapeake Bay.

Hot Tub

Kitchen

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.

Kitchen

Washer

* 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 Bay.

Hot Tub

Kitchen

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 Cecil County Public Library Chesapeake City Branch.

Kitchen

Washer

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.

Kitchen

Washer

Luxury Waterfront Home Built for Entertaining!

Abingdon MD

$846 nightly

$897 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

Located in Abingdon, this vacation home is within a 10-minute drive of Belcamp Beach and Queen Alexandra Hospital Online.

Washer

Dryer

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

Elkton MD

$265 nightly

$281 total

Dec 8 - Dec 9

Total with taxes and 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.

Kitchen

Washer

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.

Kitchen

Washer

Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic 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 Susquehanna Museum at the Lock House and Susquehanna River.

Kitchen

Washer

Wilmington Comfort 4 Min to Riverfront fenced yard

Wilmington DE

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 Mall.

Hot Tub

Kitchen

5-bedroom vacation home 5 minutes from historic Charlestown

Perryville MD

$567 nightly

$601 total

Dec 10 - Dec 11

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

A Cool Place to Stay in Wilmington DE

Wilmington DE

$150 nightly

$155 total

Dec 8 - Dec 9

Total with taxes and fees

Located in Wilmington, this vacation home is within a 15-minute drive of Wilmington Riverwalk and Christiana Mall.

Air conditioning

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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.