Visit Chester
Historic Inns of Annapolis
58 State Circle, Annapolis, MD
$145 nightly
The price is $166 total per night from Nov 9 to Nov 10
$166 total
Nov 9 - Nov 10
Total with taxes and 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 ...
8.8/10 Excellent! (1,866 reviews)
All was very good except: no soap at sink in bathroom and none could be “found.” There was a coffee pot that had to be replaced with one that could work with the type coffee pods provided. Promptly replaced, but how could housekeeping have an outdated coffee maker for older-type coffee filter ...
Reviewed on Oct 28, 2025
Graduate by Hilton Annapolis
126 West St, Annapolis, MD
$148 nightly
The price is $169 total per night from Nov 24 to Nov 25
$169 total
Nov 24 - Nov 25
Total with taxes and fees
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 ...
9.2/10 Wonderful! (1,019 reviews)
Front desk staff friendly. But there attire is not very appropriate
Reviewed on Oct 26, 2025
Country Inn & Suites by Radisson, Annapolis, MD
2600 Housley Road, Annapolis, MD
$97 nightly
The price is $110 total per night from Nov 16 to Nov 17
$110 total
Nov 16 - Nov 17
Total with taxes and fees
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! (1,012 reviews)
Country Inn and Suites, Annapolis MD
The breakfast could be better. The eggs did not taste like real eggs. Maybe the food was just not cooked right. I was pleased with it. I had to clean the hot tub before we used it.
Reviewed on Oct 27, 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 Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Chester
Book a stay at this family-friendly vacation home in Chester. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Northern Chesapeake Bay ...
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 Sep 14, 2025
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Stevensville
Book a stay at this golf vacation home in Stevensville. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Matapeake State Park and Bodkin ...
9.8/10 Exceptional! (14 reviews)
Very nice setup for larger groups, secluded and private setting . Really enjoyed our stay.
Reviewed on Oct 7, 2025
Floating 2 bed 2 bath condo stunning views of the bay
Stevensville
Stay at this houseboat in Stevensville. Enjoy a beach locale and an in-room coffeemaker. Popular attractions Matapeake State Park and Romancoke Wharf County ...
7/10 Good! (6 reviews)
Husband & I stayed during the Annapolis boat show to get a feel for what living on a yacht would be like for our year Great Loop adventure and to see what boat features would be important to us when buying. This stay suited us perfectly and Kate’s communication with us with very quick. A minor mechanical ...
Reviewed on Oct 8, 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.
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- Chesapeake Exploration Center
- Chesapeake Bay
- U.S. Naval Academy
- Chesapeake Bay Bridge
- Sandy Point State Park
- Annapolis City Dock
- Navy-Marine Corps Memorial Stadium
- Anne Arundel Medical Center
- Westfield Annapolis Mall
- St. Michaels Winery
- Rock Hall Harbor
- Annapolis Harbor Center Shopping Center
- Annapolis Maritime Museum
- Maryland Quiet Waters Park
- Annapolis Mall Shopping Center
- Maryland State House
- Queenstown Premium Outlets
- Chesapeake Bay Maritime Museum
- Annapolis Harbour Center
- Queenstown Harbor Golf Club
- William Paca House
- Chesapeake Bay Environmental Center
- Annapolis Landing Marina
- Avalon Theatre
- Ego Alley
- Eastern Neck National Wildlife Refuge
- Queenstown Harbor Golf Links