Chesapeake City Vacation Rentals

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Vacation Rentals in Chesapeake City

Sunset River Cottage

Elkton MD

Located in Elkton, this vacation home is on the waterfront, within a 15-minute drive of Chesland Park and Elk Forest Wildlife Management Area.

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

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

Perryville MD

With a stay at this vacation home in Perryville, you'll be on the waterfront, within a 5-minute drive of Chesapeake Bay and Chestnut Point Estates and Marina.

Hot Tub

Kitchen

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

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

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.

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

Havre De Grace MD

With a stay at this vacation home, you'll be centrally located in Havre De Grace, within a 5-minute drive of Chesapeake Bay and Harford Memorial Hospital.

Kitchen

Washer

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

Middletown DE

With a stay at this vacation home in Middletown, you'll be within a 5-minute drive of Middletown Historic District and The Everett Annex.

Kitchen

Washer

Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!

Chesapeake City MD

A stay at this vacation home places you in the heart of Chesapeake City, steps from Chesapeake City Bridge and South Chesapeake City Historic District.

Super cute 3 bedroom remodeled townhouse near downtown Wilmington

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.

Elegant Family Stay • Quiet Neighborhood • Comfort

New Castle DE

$353 nightly

$365 total

May 4 - May 5

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 Frightland.

Sunset River Shack -amazing waterfront view

Elkton MD

Located in Elkton, this vacation home is on the waterfront, within a 15-minute drive of Chesland Park and Elk Forest Wildlife Management Area.

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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.