Middletown Vacation Rentals

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Vacation Rentals in Middletown

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

$325 nightly

$345 total

Nov 2 - Nov 3

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 Brantwood Park and South Chesapeake City Historic District.

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

Bright & Airy Apartment w Massive Master Suite

Wilmington DE

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

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

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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.