Chestertown Vacation Rentals

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Vacation Rentals in Chestertown

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

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 14 minutes from Chesapeake Bay.

Kitchen

Washer

Private Pool & Stunning Bay Views on Kent Island

Stevensville MD

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

Pool

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 National Aquarium in Baltimore and Baltimore Convention Center.

Kitchen

Washer

Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly

Stevensville MD

When you stay at this vacation home in Stevensville, you'll be on the waterfront, just steps from Chesapeake Bay and Northern Chesapeake Bay.

Kitchen

Washer

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

Crownsville MD

$205 nightly

$233 total

Jun 22 - Jun 23

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

Cozy 2br home w/ parking in downtown Annapolis

Annapolis MD

$418 nightly

$477 total

Jun 17 - Jun 18

Total with taxes and fees

With a stay at this vacation home, you'll be centrally located in Annapolis, a 3-minute drive from U.S. Naval Academy and 12 minutes from Sandy Point State Park.

Kitchen

Washer

Hidden Fells Point Gem / Private Courtyard Patio

Baltimore MD

$191 nightly

$221 total

Jun 21 - Jun 22

Total with taxes and fees

With a stay at this vacation home, you'll be centrally located in Baltimore, within a 5-minute drive of National Aquarium in Baltimore and Baltimore Convention Center.

Kitchen

Washer

BEAUTIFULLY FURNISHED COZY ENSUITE 2BR/3BA W/ 2 SLEEPER SOFAS, UPPER FELLS POINT

Baltimore MD

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

Kitchen

Washer

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

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 6 minutes from Sandy Point State Park.

Pool

Kitchen

Waterfront Oasis w/ Private Dock, Firepit, Arcade & Sunset Views

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

Luxury 3 bed row home in the heart of downtown Fells Point

Baltimore MD

With a stay at this vacation home, you'll be centrally located in Baltimore, within a 5-minute drive of National Aquarium in Baltimore and Baltimore Convention Center.

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.