Chester
Travel Guide
Visit Chester
Waterfront Sunset Bayview: sleeps 6
Chester MD
Stay at this vacation home in Chester. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Bodkin Island and Chesapeake Bay Environmental Center ...
10/10 Exceptional! (28 reviews)
"Very nice host and beautiful modern house! Close to town and had a dock right there to sit out on and enjoy a cup or coffee! Only complaint was one shower never got hot or warm but we just used one and it was fine"
Reviewed on May 22, 2026
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Chester MD
Book a stay at this family-friendly vacation home in Chester. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Northern Chesapeake Bay ...
10/10 Exceptional! (128 reviews)
"Super wonderful stay!! Double thumbs up on all counts!"
Reviewed on May 26, 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
The price is CA $160 per night from Jun 8 to Jun 9
CA $160
CA $229 total
Jun 8 - Jun 9
includes taxes & fees
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 ...
9/10 Wonderful! (1,851 reviews)
"Always a great location and nice staff. Only reason I did not give a 5 star is because the coffee maker in the room did not work."
Reviewed on May 30, 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 vacation home in Chester. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Bodkin Island and Chesapeake Bay Environmental Center ...
10/10 Exceptional! (28 reviews)
"Very nice host and beautiful modern house! Close to town and had a dock right there to sit out on and enjoy a cup or coffee! Only complaint was one shower never got hot or warm but we just used one and it was fine"
Reviewed on May 22, 2026
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Chester MD
Book a stay at this family-friendly vacation home in Chester. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Northern Chesapeake Bay ...
10/10 Exceptional! (128 reviews)
"Super wonderful stay!! Double thumbs up on all counts!"
Reviewed on May 26, 2026
Crab Alley | Waterfront Home + Hot Tub + Game Room
Chester MD
Stay at this vacation home in Chester. Enjoy free WiFi, laundry facilities, and a pool table. Popular attractions Bodkin Island and Chesapeake Bay Environmental ...
10/10 Exceptional! (1 review)
"Beautiful place !"
Reviewed on Mar 31, 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 at Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants.
Things to do
2 Hour Chesapeake Day Sail on Catamaran Epiphany
CA $335
per adult
2-Hour Relaxing Chesapeake Day Sail on Lady Patty
CA $219
per adult
