Visit Chester
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 ...
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
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
$76 nightly
The price is $87 total per night from Dec 28 to Dec 29
$87 total
Dec 28 - Dec 29
Total with taxes and fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ...
8.6/10 Excellent! (1,013 reviews)
Great
Reviewed on Dec 9, 2025
Historic Inns of Annapolis
58 State Circle Annapolis MD
$164 nightly
The price is $187 total per night from Dec 21 to Dec 22
$187 total
Dec 21 - Dec 22
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! (1,898 reviews)
Beautiful area! Loved the room! We took a taxi from the airport, it was nice to not have to worry about parking.
Reviewed on Dec 11, 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 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 ...
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
Floating 2 bed 2 bath condo stunning views of the bay
Stevensville MD
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
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Annapolis MD
Stay at this vacation home in Annapolis. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Sandy Point State Park and Bay Hills Golf ...
9.8/10 Exceptional! (39 reviews)
Perfect place for a family get together. So much to do. Great kitchen. Comfortable beds and bed rooms.
Reviewed on Nov 4, 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
- U.S. Naval Academy
- Navy-Marine Corps Memorial Stadium
- Chesapeake Bay
- Anne Arundel Medical Center
- Annapolis City Dock
- Chesapeake Bay Bridge
- Annapolis Mall Shopping Center
- Sandy Point State Park
- Westfield Annapolis Mall
- Annapolis Harbor Center Shopping Center
- Maryland State House
- Annapolis Maritime Museum
- Maryland Quiet Waters Park
- Queenstown Premium Outlets
- St. Michaels Winery
- Rock Hall Harbor
- Maryland Hall for Creative Arts
- Chesapeake Bay Maritime Museum
- Avalon Theatre
- William Paca House
- Northern Chesapeake Bay
- Queenstown Harbor Golf Club
- Annapolis Landing Marina
- Thurgood Marshall Memorial
- Annapolis Harbour Center
