Chestertown Vacation Rentals

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Vacation Rentals in Chestertown

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

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Annapolis MD

A stay at this vacation home places you in the heart of Annapolis, within a 10-minute walk of U.S. Naval Academy and Ellen O. Moyer Nature Park at Back Creek.

Kitchen

Washer

Large 2 bedroom house with private parking in a nice neighborhood

Arnold MD

$287 nightly

$327 total

Dec 9 - Dec 10

Total with taxes and fees

With a stay at this vacation home in Arnold, you'll be within a 15-minute drive of U.S. Naval Academy and Severna Park Golf Center.

Kitchen

Washer

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Annapolis MD

$1,134 nightly

$1,292 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

This vacation home is in the heart of Annapolis, within a 10-minute walk of Maynard-Burgess House and U.S. Naval Academy.

Kitchen

Washer

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

Annapolis MD

With a stay at this vacation home, you'll be centrally located in Annapolis, within a 5-minute drive of U.S. Naval Academy and Annapolis Harbor.

Pool

Kitchen

Charming garden row home, easy 4 block walk to the heart of Annapolis.

Annapolis MD

With a stay at this vacation home in Annapolis (Historic District), you'll be within a 5-minute walk of U.S. Naval Academy and Hammond-Harwood House.

Kitchen

Washer

Location is perfect and a big bonus we have our own parking at the home!

Annapolis MD

With a stay at this vacation home in Annapolis (Historic District), you'll be within a 10-minute walk of U.S. Naval Academy and 97, 99 and 101 East Street.

Kitchen

Washer

BEAUTIFULLY FURNISHED COZY ENSUITE 2BR3 BA IN UPPER FELLS POINT, BALTIMORE

Baltimore MD

With a stay at this vacation home in Baltimore (Upper Fells Point), you'll be within a 5-minute drive of Johns Hopkins Hospital and National Aquarium in Baltimore.

Kitchen

Washer

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Pasadena MD

Located in Pasadena, this vacation home is on the waterfront, within a 10-minute drive of Fort Smallwood Park and Compass Pointe Golf Courses.

Kitchen

Washer

* 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

Waterfront Oasis w/ Private Dock, 3BR/2BA

Middle River MD

Located in Middle River, this vacation home is on the waterfront, within a 15-minute drive of Johns Hopkins Medicine and White Marsh Mall.

Kitchen

Pet friendly

200 steps to the beach!

Rock Hall MD

With a stay at this vacation home in Rock Hall, you'll be just steps from Chesapeake Bay and Northern Chesapeake Bay.

Kitchen

Washer

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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.