Chestertown Vacation Rentals

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Vacation Rentals in Chestertown

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

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

Historic Home with Parking Steps From Capital & USNA

Annapolis MD

This vacation home is in the heart of Annapolis, within a 5-minute walk of The Colonial Players and U.S. Naval Academy.

Kitchen

Washer

5-bedroom vacation home 5 minutes from historic Charlestown

Perryville MD

$494 nightly

$524 total

Mar 9 - Mar 10

Total with taxes and fees

Located in Perryville, this vacation home is on the waterfront, within a 5-minute drive of Chestnut Point Estates and Marina and Craft Haven Marina.

Kitchen

Washer

BALTIMORE ROWHOUSE CLOSE TO WATER KING BED PARKING

Baltimore MD

With a stay at this vacation home, you'll be centrally located in Baltimore, a 4-minute drive from Johns Hopkins Hospital and 7 minutes from Oriole Park at Camden Yards.

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

240' Private Beachfront @Kent Island Love Point - Great for Families

stevensville MD

Located in Stevensville, this vacation home is on the waterfront, within a 5-minute drive of Love Point State Park and Chesapeake Bay.

Kitchen

Washer

Cute, Cozy 2-bedroom house in near Annapolis with water access

Crownsville MD

$191 nightly

$218 total

Mar 16 - Mar 17

Total with taxes and fees

With a stay at this vacation home in Crownsville (Herald Harbor), you'll be a 4-minute drive from Joyces Marina and 9 minutes from Eisenhower Golf Course.

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 within a 15-minute drive of U.S. Naval Academy and Chesapeake Bay.

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Kitchen

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

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

Timeless Charm Meets Modern Comfort

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 William Paca House.

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.