Chester
Travel Guide
Visit Chester
Waterfront Sunset Bayview: sleeps 6
Chester MD
Stay at this holiday home in Chester. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Bodkin Island and Chesapeake Bay Environmental Center ...
10/10 Exceptional! (26 reviews)
"We loved our stay at this gorgeous waterfront property in Chester! The home is clean and bright with many gathering spaces for our group of five. We really enjoyed spending time on the back porch on the comfy couches enjoying the beautiful view or sitting around the large dining table eating and ..."
Reviewed on 21 Apr 2026
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 ...
10/10 Exceptional! (126 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
Historic Inns of Annapolis
58 State Circle Annapolis MD
The price is €144 per night from 31 May to 1 Jun
€144
31 May - 1 Jun
includes taxes & fees
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! (1,851 reviews)
"Very helpful staff, nice ambiance"
Reviewed on 18 May 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 Sunset Bayview: sleeps 6
Chester MD
Stay at this holiday home in Chester. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Bodkin Island and Chesapeake Bay Environmental Center ...
10/10 Exceptional! (26 reviews)
"We loved our stay at this gorgeous waterfront property in Chester! The home is clean and bright with many gathering spaces for our group of five. We really enjoyed spending time on the back porch on the comfy couches enjoying the beautiful view or sitting around the large dining table eating and ..."
Reviewed on 21 Apr 2026
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 ...
10/10 Exceptional! (126 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
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 ...
10/10 Exceptional! (53 reviews)
"Absolutely Lovely, Julia was very sweet and the home had everything you could have thought of or forgotten to bring."
Reviewed on 13 Apr 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.
