Chester, MD

Travel Guide

A coastal town with a marina, a bridge, and a highway.
A calm lake with reflections of the sky, surrounded by a forested area.
A boat docked at a pier during twilight with a city skyline in the background.
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
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Historic Inns of Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
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Crowne Plaza Annapolis by IHG
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3 out of 5
170 Admiral Cochrane Dr Edgewater MD
Book a stay at this business-friendly hotel in Edgewater. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the clean ...
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Sonesta ES Suites Annapolis
See all 1,210 properties in Chester
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.

Stay near popular Chester attractions

Chesapeake Exploration Center

Learn about the events happening at Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants.
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Things to do

St Michaels Cruise from Annapolis with Museum Entry

Day on the Bay Cruise from Annapolis to St Michaels

$157
per adult
Day on the Bay Cruise from Annapolis to St Michaels
St. Michaels: 2-Hour Relaxing Chesapeake Sail on Epiphany

St. Michaels: 2-Hour Relaxing Chesapeake Sail on Epiphany

$270
per adult
St. Michaels: 2-Hour Relaxing Chesapeake Sail on Epiphany
Epiphany

2 Hour Chesapeake Day Sail on Catamaran Epiphany

$245
per adult
2 Hour Chesapeake Day Sail on Catamaran Epiphany
St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty

St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty

$159
per adult
St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty
St. Michaels: 2-Hour Wine Tasting on Sailing Cruise Epiphany

St. Michaels: 2-Hour Wine Tasting on Sailing Cruise Epiphany

$298
per adult
St. Michaels: 2-Hour Wine Tasting on Sailing Cruise Epiphany
2-Hour Relaxing Chesapeake Day Sail on Lady Patty

2-Hour Relaxing Chesapeake Day Sail on Lady Patty

$160
per adult
100% of travellers recommend
2-Hour Relaxing Chesapeake Day Sail on Lady Patty
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Cities near Chester

A large suspension bridge spanning a wide river with a clear sky above.

Grasonville

A pier extending into a body of water with people fishing, a clear sky, and distant land with a bridge.

Stevensville