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Locality

Chestertown

10 locals recommend

Tips from locals

Bob And Beth
Bob And Beth
July 23, 2020
The Chestertown downtown waterfront is a great place to walk, dine, and go back in history. There are many colonial homes, and the Riverwalk has park benches where you can sit and enjoy the view. The Sultana, an historic replica an American schooner that was captured by the British during the…
Bob
Bob
July 21, 2020
Living working historic town on the Chester River. Tree lined brick sidewalks with unique shopping and dining.
John
John
January 7, 2020
Chestertown, the county seat of Kent, the Eastern Shore of Maryland's oldest county, was founded in 1706 and served as a major port of entry during colonial times. Its brick sidewalks and attractive antique stores, restaurants and inns beckon visitors and residents alike to wander, browse and…
Jim And Gale
Jim And Gale
September 22, 2019
Chestertown is an historic small town on the majestic, unspoiled Chester River on Maryland's famous Eastern Shore. It has been since 1782 the home of Washington College. Many shops, restaurants, and bars are within walking distance, and a short drive through the surrounding farmland will take the…
Jim
Jim
June 29, 2019
Chestertown is a 20 minute drive from Rock Hall. Great Farmers' Market on Saturday Morning!

Places to stay nearby

SUPERHOST
  1. Entire house
  2. 8 beds
Duchess of Kent: Walk to downtown & College
SUPERHOST
  1. Entire flat
  2. 1 bed
Carriage House Hideaway in Middle of Chestertown
SUPERHOST
  1. Private room
  2. 3 beds
Chestertown - Eastern Shore Getaway
  1. Entire house
  2. 4 beds
Merry Manor Pet Friendly Home
SUPERHOST
  1. Entire house
  2. 6 beds
Wren Retweet- Country Estate in Center of C’Town
SUPERHOST
  1. Entire guest house
  2. 1 bed
Cozy Carriage House
  1. Entire flat
  2. 1 bed
Downtown Studio Apartment
  1. Entire flat
  2. 2 beds
The Bittersweet
SUPERHOST
  1. Entire house
  2. 3 beds
Town House in the Heart of Chestertown
No reviews yet
  1. Entire house
  2. 3 beds
Historic house on High Street, Chestertown, MD
SUPERHOST
  1. Entire house
  2. 7 beds
Classic Victorian in Chestertown
SUPERHOST
  1. Private room
  2. 1 bed
A Simple Stay...next door to Washington College
  1. Private room
  2. 2 beds
Private Room w/bath: Walk to Washington College
  1. Entire house
  2. 5 beds
Quiet, Charming, home in downtown Chestertown
  1. Entire house
  2. 7 beds
The Patriot House-Chestertown, MD
SUPERHOST
  1. Private room
  2. 1 bed
Another Simple Stay...next door to WAC
Location
Chestertown, Maryland 21620