Chester Travel Guide
Tourist Guide
Visit Chester
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Chester MD
Stay at this family-friendly holiday home in Chester. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Northern Chesapeake Bay and Matapeake ...
9.8/10 Exceptional! (94 reviews)
Perfect vacation home....large and comfortable.....relaxing, peaceful, close to bike trails, a great homebase for sightseeing many small towns...loved meeting the homeowner, very friendly..
Reviewed on 14 Sept 2025
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
The price is AU$127 per night from 8 Feb to 9 Feb
AU$127
8 Feb - 9 Feb
includes taxes & fees
Stay at this business-friendly hotel in Annapolis. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the restaurant and the helpful ...
8.6/10 Excellent! (1,000 reviews)
Clean and we moved to a quiet room as well
Reviewed on 8 Jan 2026
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
The price is AU$181 per night from 18 Feb to 19 Feb
AU$181
18 Feb - 19 Feb
includes taxes & fees
Stay at this business-friendly hotel in Annapolis. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (1,006 reviews)
Nice hotel
Reviewed on 18 Jan 2026
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.
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Chester MD
Stay at this family-friendly holiday home in Chester. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Northern Chesapeake Bay and Matapeake ...
9.8/10 Exceptional! (94 reviews)
Perfect vacation home....large and comfortable.....relaxing, peaceful, close to bike trails, a great homebase for sightseeing many small towns...loved meeting the homeowner, very friendly..
Reviewed on 14 Sept 2025
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Annapolis MD
Stay at this holiday home in Annapolis. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Hammond-Harwood House and French Soldiers Monument ...
10/10 Exceptional! (126 reviews)
Great location & host.
Reviewed on 28 Dec 2025
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Saint Michaels MD
Stay at this cottage in St. Michaels. Enjoy a garden, laundry facilities and patios. Popular attractions Muskrat Park and Higgins Yacht Yard and Marina are located ...
9.6/10 Exceptional! (189 reviews)
Great house right in the heart of town!
Reviewed on 3 Jan 2026
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.
Popular places to visit
Chesapeake Exploration Center
Learn about the events happening in Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants.
