Middletown Vacation Rentals

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Vacation Rentals in Middletown

* 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.

Sunset River Cottage

Elkton MD

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

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.

Woodland Retreat at Fair Hill- Hot Tub, Pool, and Sport Court

Elkton MD

$1,469 nightly

$1,480 total

Sep 8 - Sep 9

Total with taxes and fees

Located in Elkton, this vacation home is on a river, within a 15-minute drive of Fair Hill Equestrian Center and Milburn Stone Theater.

Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge

Charlestown MD

When you stay at this vacation home in Perryville, you'll be on the waterfront, within a 15-minute walk of Charlestown Town Hall and Fair Green Park.

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 Brantwood Park and Chesapeake City Bridge.

Kitchen

Washer

Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

Chesapeake City MD

When you stay at this vacation home in Chesapeake City, you'll be on the beach, within a 5-minute drive of Two Rivers Yacht Basin and Bohemia Vista Marina.

Sunset River Shack -amazing waterfront view

Elkton MD

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

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.

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Elkton MD

With a stay at this vacation home in Elkton, you'll be within a 15-minute drive of Chesapeake Bay and Upper Bay Museum.

Right in the center of everywhere in Dover

Dover DE

With a stay at this vacation home in Dover, you'll be within a 10-minute drive of Dover International Speedway and Williams Park.

Kitchen

Washer

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 Upper Bay Museum.

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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.