Visit Chester
Historic Inns of Annapolis
58 State Circle, Annapolis, MD
The price is CA $223 per night from May 8 to May 9
CA $223
CA $302 total
includes taxes & fees
May 8 - May 9
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 ...
8.8/10 Excellent! (1,757 reviews)
"We had an undesirable use of the shower. It was extremely small and without a reomoveable showerhead therefore making it impossible to bathe and rinse. At the least if there was a removeable wand/shower handle it would allow for a short person to have the spray hit more than just the top of their ..."
Reviewed on Apr. 29, 2025
Graduate by Hilton Annapolis
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is CA $233 per night from May 27 to May 28
CA $233
CA $265 total
includes taxes & fees
May 27 - May 28
Stay at this 4-star business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and ...
9.4/10 Exceptional! (1,001 reviews)
Service and accommodation top notch!
"Second time staying here. Hotel is beautiful. This time we were staying for 2 nights and the first night, the room smelled of mold or mildew as soon as I opened the door. Not sure what was going on, but I called the front desk in the am. They happily accommodated our request to be moved. We were ..."
Reviewed on Apr. 29, 2025
Country Inn & Suites by Radisson, Annapolis, MD
2600 Housley Road, Annapolis, MD
The price is CA $134 per night from May 8 to May 9
CA $134
CA $153 total
includes taxes & fees
May 8 - May 9
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,002 reviews)
"Wonderful staff!"
Reviewed on Apr. 29, 2025
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
Stay at this vacation home in Chester. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Bodkin Island and Chesapeake Bay Environmental ...
10/10 Exceptional! (13 reviews)
Lovely clean home and nice yard.
"Really great spot, the house was very clean and new. We had nice weather and spent a lot of time outside and in the enclosed sun room."
Reviewed on Apr. 20, 2025
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Annapolis
Book a stay at this family-friendly vacation home in Annapolis. Enjoy free WiFi, a water park, and patios. Popular attractions John Smith House and Annapolis ...
10/10 Exceptional! (195 reviews)
Great weekend with family!
"The communication was awesome! Beds were comfortable. Location is the best for USNA and walking to restaurants and shops in Annapolis. House is very charming with many amenities."
Reviewed on Apr. 29, 2025
The Blue Crab Beach House - Free beach passes
North Beach
Stay at this vacation home in North Beach. Enjoy free WiFi, a water park, and a garden. Popular attractions Bayside History Museum and Chesapeake Beach Water ...
10/10 Exceptional! (53 reviews)
Great location and clean!
"Came for a wedding at Herrington on the Bay which was only a 5 minute drive away. Short walk to the beach and many restaurants in North Beach. Great for 4 people."
Reviewed on Apr. 26, 2025
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.