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 NZ$156 per night from 22 Feb to 23 Feb
NZ$156
22 Feb - 23 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! (1,001 reviews)
The staff were so nice and helpful and the amenities were great. The restaurant and bar were great especially the breakfast and of course the cookies. The shuttle was so convenient, fast, and super polite. Great stay. I recommend and will stay again next time I'm in town.
Reviewed on 11 Feb 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
Stay at this historic hotel in Annapolis. Enjoy free Wi-Fi, room service and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,877 reviews)
We had a wonderful stay and really enjoyed it. The courtesy of the stuff was outstanding!
Reviewed on 13 Feb 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
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Annapolis MD
Stay at this holiday home in Annapolis. Enjoy free Wi-Fi, private pools and breakfast (surcharge). Our guests praise the pool in their reviews. Popular attractions ...
10/10 Exceptional! (129 reviews)
Great host! Great house!
Reviewed on 2 Jan 2026
Chesapeake Houseboat Getaway on Kent Island, Maryland
Stevensville MD
Stay at this houseboat in Stevensville. Enjoy patios, an in-room coffee maker and in-room fireplaces. Popular attractions Romancoke Wharf County Park and Matapeake ...
9.8/10 Exceptional! (45 reviews)
It was magical walking up to the water each morning. It was cold outside but so cozy inside. And the host was outstanding very accommodating and friendly.
Reviewed on 25 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.
