Chesapeake City Vacation Rentals

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Vacation Rentals in Chesapeake City

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.

Hot Tub

Kitchen

Sunset River Cottage

Elkton MD

Located in Elkton, this vacation home is on the waterfront, within a 10-minute drive of Chesland Park and Brantwood Park.

Hot Tub

Kitchen

5BR Chesapeake Waterfront Estate with Private Dock

Perryville MD

With a stay at this vacation home in Perryville, you'll be within a 15-minute walk of Chesapeake Bay and Northern Chesapeake Bay.

Kitchen

Washer

HISTORIC WATERFRONT 2 Bedrooms/4 beds in Chesapeake City with AC

Chesapeake City MD

$275 nightly

$292 total

Oct 7 - Oct 8

Total with taxes and fees

When you stay at this vacation home in Chesapeake City, you'll be on the waterfront, within a 5-minute drive of Chesapeake City Bridge and Brantwood Park.

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

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 Center.

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

Nancy’s Touch, A Waterfront Paradise!

North East MD

With a stay at this vacation home in North East, you'll be on the waterfront, within a 15-minute drive of Chesapeake Bay and Chesapeake Bay Golf Club.

Kitchen

Washer

Waterfront House on the Upper Chesapeake Bay

Elkton MD

Located in Elkton, this vacation home is on the waterfront, a 5-minute drive from Chesland Park and 7 minutes from Brantwood Park.

Kitchen

Free WiFi

Tip Of The Town Fresh and New 3 Bedroom Nest

North East MD

With a stay at this vacation home in North East, you'll be within a 15-minute drive of Chesapeake Bay and North East Community Park.

Kitchen

Washer

White Clay Creek Cottage

Newark DE

Located in Newark, this vacation home is within a 15-minute drive of University of Delaware and Delaware Park Racetrack and Slots.

Kitchen

Pet friendly

Amazing Waterfront Home on the Bush River

Edgewood MD

When you stay at this vacation home in Edgewood, you'll be on the waterfront and 9 minutes by car from CopperPlex.

Kitchen

Washer

Don't see what you're looking for?

See all available properties in Chesapeake City

View all properties

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.