Chestertown Vacation Rentals

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Vacation Rentals in Chestertown

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 Chesapeake Bay and Annapolis City Dock.

Pool

Kitchen

Sailor's Sunrise Cottage - Chesapeake Bay

Perryville MD

When you stay at this vacation home in Perryville, you'll be on the waterfront, within a 10-minute walk of Chesapeake Bay and Northern Chesapeake Bay.

Hot Tub

Kitchen

3-bedroom Townhome in Exciting Corner of Fells Point!

Baltimore MD

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

Kitchen

Washer

Waterfront Retreat home with Deck, Dock & Sunset Views. Your Marley Creek Escape

Glen Burnie MD

$244 nightly

$278 total

Oct 18 - Oct 19

Total with taxes and fees

With a stay at this vacation home in Glen Burnie (Marley), you'll be within a 15-minute drive of Arundel Mills Mall and Maryland Live Casino.

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, steps from Annapolis City Dock and 4 minutes by foot from U.S. Naval Academy.

Charming Historic Annapolis Home With Two Off-street Parking Places!

Annapolis MD

With a stay at this vacation home, you'll be centrally located in Annapolis, just a 4-minute walk from Annapolis City Dock and 8 minutes by foot from U.S. Naval Academy.

Luxury 3-bed Townhome W/Modern finishes & Easy access to Baltimore &Annapolis.

Glen Burnie MD

$328 nightly

$374 total

Sep 21 - Sep 22

Total with taxes and fees

With a stay at this vacation home in Glen Burnie (Ferndale), you'll be within a 15-minute drive of M&T Bank Stadium and Oriole Park at Camden Yards.

Kitchen

Washer

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

Crownsville MD

$195 nightly

$222 total

Oct 19 - Oct 20

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

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Annapolis MD

A stay at this vacation home places you in the heart of Annapolis, steps from U.S. Naval Academy and Annapolis City Dock.

Kitchen

Washer

Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.

Baltimore MD

With a stay at this vacation home in Baltimore (Canton), you'll be within a 5-minute drive of Baltimore Convention Center and Johns Hopkins Hospital.

Hot Tub

Kitchen

Peaceful Pet-Friendly Stay - Near USNA and Beaches

Annapolis MD

With a stay at this vacation home, you'll be centrally located in Annapolis, a 4-minute drive from Chesapeake Bay and 13 minutes from Annapolis City Dock.

Hudson house

3037 Hudson St Baltimore MD

With a stay at this vacation home in Baltimore (Canton), you'll be a 5-minute drive from Johns Hopkins Hospital and 7 minutes from Baltimore Convention Center.

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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.