Beginning of main content

Get 24/7 travel help, thanks to our Customer First Guarantee

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Tonight Dec 10 - Dec 11
This weekend Dec 13 - Dec 15
Next weekend Dec 20 - Dec 22

Most Frequently Booked Chester Hotels

Get Rates
Sunsets on Crab Alley

Sunsets on Crab Alley

Chester, MD
Situated on the waterfront, this romantic vacation home is within 12 mi (20 km) of Chesapeake Bay Environmental Center, Chesapeake Bay Bridge, and Queenstown Harbor Golf Links. Queenstown Harbor Golf Club and Sandy Point State Park are also within 12 mi (20 km).
Graduate Annapolis

Graduate Annapolis

4.0 out of 5.0 126 West St, Annapolis, MD
(31 Reviews)
This hotel features a restaurant, a 24-hour fitness center, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, a terrace, and limo/town car service are also offered.
Crowne Plaza Annapolis

Crowne Plaza Annapolis

3.5 out of 5.0 173 Jennifer Rd, Annapolis, MD
(36 Reviews)
This hotel features an indoor pool, a 24-hour fitness center, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the spa tub and perks like free self parking.

How much is a hotel room in Chester?

Hotels in Chester start at $85 per night. Prices and availability subject to change. Additional terms may apply.

Chester Hotel & Travel Guide

If you are traveling about in Annapolis and feel like having a look around in Chester, there are a select variety of lodgings. Travelocity's travel guide presently lists 6 places to stay in and around the city center.

Learn about a few accommodation options that are within a short drive of Chester's urban center, such as the Historic Kent Manor Inn and Hilton Garden Inn Kent Island.

Have a look at the Inn at Perry Cabin by Belmond and also the Annapolis Waterfront Hotel, Autograph Collection. The Inn at Perry Cabin by Belmond is positioned 13 miles (21 kilometers) outside of the heart of Chester. The Annapolis Waterfront Hotel, Autograph Collection, is located just 11 miles (18 kilometers) away. Another possibility is to take a room at the Five Gables Inn and Spa or the Loews Annapolis Hotel.

If you have some spare time, you should travel further in the Central Maryland region. Central Maryland offers coastal plains, and other interesting tourist sites include street art. In this area of United States of America adventurous travelers may partake in shore fishing.

The nearest accommodations in Annapolis include Bowie and Arnold. Bowie is 25 miles (41 kilometers) to the west of Chester, while Arnold is 13 miles (20 kilometers) to the west. Bowie Travelocity-listed accommodations include the TownePlace Suites Bowie Town Center and Comfort Inn Conference Center. The Comfort Inn Annapolis and Village Inn are amongst the hotel establishments in Arnold.

Simply because you and your traveling partners are having a getaway, who's to say you shouldn't expand your passion for a day of sports. You will find Nationals Park 40 miles (64 kilometers) to the west of Chester. Those that wish to stay nearby can explore the The Jefferson, Washington, DC or the Marriott Marquis Washington, DC.

Baltimore Washington International Thurgood Marshall Airport is a practical entry point for accessing Chester. You can find it 25 miles (41 kilometers) from the downtown area. For travelers who would find it convenient to stay nearby, book the Residence Inn by Marriott Baltimore BWI Airport or BWI Airport Marriott.

Recent Chester Hotel Reviews By Fellow Wanderers

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.