Chestertown Vacation Rentals

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Vacation Rentals in Chestertown

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

Annapolis MD

With a stay at this vacation home, you'll be centrally located in Annapolis, a 1-minute drive from U.S. Naval Academy and 12 minutes from Chesapeake Bay Bridge.

Kitchen

Washer

5-bedroom vacation home 5 minutes from historic Charlestown

Perryville MD

$495 nightly

$525 total

Apr 29 - Apr 30

Total with taxes and fees

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.

Captivating Chesapeake experience

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.

Kitchen

Washer

Historic Annapolis Home 1.5 blocks from center of town.

Annapolis MD

A stay at this vacation home places you in the heart of Annapolis, within a 15-minute walk of U.S. Naval Academy and Spa Creek.

Kitchen

Washer

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

Easton MD

When you stay at this vacation home in Easton, you'll be on the waterfront and 14 minutes by car from Hog Neck Golf Course.

Pool

Kitchen

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.

Walking distance to Navy Stadium! No cleaning fees!

Annapolis MD

With a stay at this vacation home in Annapolis (West Annapolis), you'll be within a 15-minute drive of U.S. Naval Academy and Chesapeake Bay Bridge.

Kitchen

Washer

Charming Historic Townhouse Steps From USNA

Annapolis MD

With a stay at this vacation home, you'll be centrally located in Annapolis, a 1-minute drive from U.S. Naval Academy and 13 minutes from Chesapeake Bay.

Kitchen

Washer

Historic Home with Parking Steps From Capital & USNA

Annapolis MD

With a stay at this vacation home, you'll be centrally located in Annapolis, a 1-minute drive from U.S. Naval Academy and 12 minutes from Chesapeake Bay Bridge.

Kitchen

Washer

Glen Burnie Escape - Pet friendly with easy access to multiple attractions.

Glen Burnie MD

$339 nightly

$386 total

Apr 28 - Apr 29

Total with taxes and fees

With a stay at this vacation home in Glen Burnie, you'll be within a 15-minute drive of Baltimore Cruise Terminal and Arundel Mills Mall.

Kitchen

Washer

Historic Downtown House with Off Street Parking

Annapolis MD

A stay at this vacation home places you in the heart of Annapolis, within a 15-minute walk of U.S. Naval Academy and Maynard-Burgess House.

Kitchen

Washer

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Annapolis MD

With a stay at this vacation home in Annapolis (Cape Saint Claire), you'll be a 2-minute drive from Chesapeake Bay and 7 minutes from Chesapeake Bay Bridge.

Pool

Kitchen

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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.