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Your Chestertown Vacation
There's no better way to embark on an adventure than with one of our vacation packages to Chestertown. The colonial history and cultural experiences are just two of the countless reasons to spend some time in this captivating city. Fill your free time with visits to Washington College, Rolphs Wharf Marina and Garfield Center for the Arts at the Prince Theater, some of the things you simply have to see during a trip to Chestertown. A couple of quick clicks is all it takes to put together a tailor-made Chestertown vacation on Expedia.
The Latest Chestertown vacation packages

White Marlin Inn
Reviewed on Jul 6, 2025

Bay Club Resort by Coolvacay
Reviewed on Jul 2, 2025


The Surf Shanty Motel
Reviewed on Jul 5, 2025

Discover the most popular places to visit in Chestertown
Washington College
Take a campus tour or just explore the area of Washington College, during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
Rolphs Wharf Marina
Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.
Historical Society of Kent County Maryland
You can spend an afternoon exploring the galleries in Historical Society of Kent County Maryland during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
Chestertown Hotel Deals

Reviewed on Jul 1, 2025

Reviewed on Jul 3, 2025

Reviewed on Jun 22, 2025
Find the Best Chestertown Vacation Packages
Chestertown Essential Information
Language | English |
---|---|
Currency | U.S dollars |
Population | 5,100 |
Max Temp Winter | 45ºF |
Max Temp Summer | 80ºF |
Top Sights | Waterman’s Museum, Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater |
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- Hotels near Washington College
- Hotels near River Arts Chestertown
- Hotels near Historical Society of Kent County Maryland
- Hotels near Garfield Center for the Arts at the Prince Theater
- Hotels near Wilmer Park
- Hotels near Rolphs Wharf Marina
- Worton Hotels
- Motels in Worton
- Church Hill Hotels
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- Kennedyville Hotels
- 4 Star Hotels in Kennedyville
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- B&B in Still Pond
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- Price Hotels
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- Hotels near The Mainstay
- Hotels near Betterton Beach
- Hotels near Rock Hall Harbor
- Washington College
- River Arts Chestertown
- Historical Society of Kent County Maryland
- Garfield Center for the Arts at the Prince Theater
- Wilmer Park
- Rolphs Wharf Marina
- Worton Vacations
- Visit Worton
- Cassinelli Winery and Vineyards
- Visit Church Hill
- Visit Kennedyville
- Visit Still Pond
- Visit Great Oak Landing
- Visit Crumpton
- Rock Hall Vacations
- The Mainstay
- Visit Betterton
- Visit Rock Hall
- Rock Hall Harbor
- Waterman’s Museum
- Tilmon's Island Winery
- Car rentals near Worton
- Car rentals near Pomona
- Car rentals near Fairlee
- Car rentals near Georgetown
- Car rentals near Church Hill
- Car rentals near Great Oak Landing
- Car rentals near Crumpton
- Car rentals near Crumpton Auction
- Car rentals near Edesville
- Car rentals near Tolchester Beach
- Car rentals near Price
- Car rentals near Betterton
- Car rentals near Rock Hall
- Avis Rental Cars in Rock Hall