Visit Chester
Historic Inns of Annapolis
58 State Circle, Annapolis, MD
$145 nightly
The price is $166 total per night from Nov 16 to Nov 17
$166 total
Nov 16 - Nov 17
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! (1,874 reviews)
Beautiful
Reviewed on Nov 5, 2025
Country Inn & Suites by Radisson, Annapolis, MD
2600 Housley Road, Annapolis, MD
$93 nightly
The price is $106 total per night from Dec 7 to Dec 8
$106 total
Dec 7 - Dec 8
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! (1,007 reviews)
Came in late at night and left early the Inn was quiet, safe, comfortable and clean. Ice maker on 1st floor was out of order but there is a second one. Staff was attentive and helpful when we came in and check in was quick and easy. Would stay here again for other local sporting events.
Reviewed on Nov 8, 2025
Sonesta ES Suites Annapolis
170 Admiral Cochrane Dr, Edgewater, MD
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $95 total per night from Nov 30 to Dec 1
$95 total
Nov 30 - Dec 1
Total with taxes and fees
Book a stay at this business-friendly hotel in Edgewater. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (940 reviews)
All of the above and more. Spotless room and extraordinary staff!
Reviewed on Nov 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.
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
- Annapolis Harbor Center Shopping Center
- Maryland Quiet Waters Park
- Annapolis Mall Shopping Center
- Maryland State House
- Annapolis Maritime Museum
- Chesapeake Bay Maritime Museum
- Queenstown Premium Outlets
- Annapolis Harbour Center
- Queenstown Harbor Golf Club
- Rock Hall Harbor
- Chesapeake Bay Environmental Center
- William Paca House
- Annapolis Landing Marina
- Avalon Theatre
- Ego Alley
- Eastern Neck National Wildlife Refuge
- Maryland Hall for Creative Arts