Middletown Vacation Rentals

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Vacation Rentals in Middletown

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

Charming 2-bedroom house with WiFi, AC in marvelous Wilmington

Wilmington DE

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

Kitchen

Washer

Fox Field Cottage in Arden | 10 min to Riverfront

Wilmington DE

With a stay at this vacation home in Wilmington, you'll be within a 15-minute drive of Wilmington Riverwalk and Brandywine Valley.

Kitchen

Pet friendly

* 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

Cozy Farmhouse in Greenville, DE

Wilmington DE

With a stay at this vacation home in Wilmington, you'll be within a 15-minute drive of Longwood Gardens and Wilmington Riverwalk.

Kitchen

Washer

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

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

Elkton MD

$265 nightly

$281 total

Dec 7 - Dec 8

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

Charming 3-bedroom house with AC and WiFi in lovely 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.

Washer

Dryer

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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.