Chestertown Vacation Rentals

Name: Amazing Modern house with a full kitchen and parking
Address: Smyrna

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Vacation Rentals in Chestertown

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

$629

per night

Jun 4 - Jun 5

With a stay at this vacation home in Annapolis (Cape Saint Claire), you'll be within a 10-minute drive of Sandy Point State Park and Chesapeake Bay Bridge.

Pool

Pet friendly

Caribbean Pool Home <1 mile from Matapeake Beach!

$227

per night

May 28 - May 29

When you stay at this vacation home in Stevensville, you'll be near the beach and 7 minutes by foot from Matapeake State Park.

Pool

Pet friendly

Directly Across from Gate One & Steps from the Waterfront

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 Sandy Point State Park.

Pet friendly

Fireplace

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

Located in Chestertown, this vacation home is on the waterfront, within a 15-minute drive of Washington College and Garfield Center for the Arts at the Prince Theater.

Charming Charles Retreat- The perfect space for fun and relaxation!

With a stay at this vacation home, you'll be centrally located in Annapolis, a 2-minute drive from U.S. Naval Academy and 12 minutes from Chesapeake Bay Bridge.

Air conditioning

Washer

Suburban Retreat Near Baltimore Harbor

With a stay at this vacation home in Baltimore (Brooklyn), you'll be within a 15-minute drive of Baltimore Cruise Terminal and Oriole Park at Camden Yards.

Relax on Kent Island in 3 Bedroom Home w/Waterview

$100

per night

May 27 - May 28

Located in Stevensville, this vacation home is within a 15-minute drive of Matapeake State Park and Paul Reed Smith Guitars.

Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.

When you stay at this vacation home in Worton, you'll be on the waterfront and 11 minutes by car from Betterton Beach.

Charming Historic Townhouse Steps From USNA

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 Sandy Point State Park.

Free parking Historic Union House Downtown with private patio

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 Bridge.

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

With a stay at this vacation home, you'll be centrally located in Annapolis, a 2-minute drive from U.S. Naval Academy and 12 minutes from Chesapeake Bay Bridge.

Amazing Modern house with a full kitchen and parking

With a stay at this vacation home in Smyrna, you'll be within a 15-minute drive of Bayhealth Emergency Center - Smyrna and Delaware State Police Museum and Education 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.