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
$75 nightly
The price is $85 total per night from Jan 4 to Jan 5
$85 total
Jan 4 - Jan 5, 2026
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! (1,021 reviews)
Overall great experience
Reviewed on Dec 23, 2025
Historic Inns of Annapolis
58 State Circle Annapolis MD
$169 nightly
The price is $193 total per night from Jan 1 to Jan 2
$193 total
Jan 1 - Jan 2, 2026
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! (1,907 reviews)
Best place to stay is the main building
Reviewed on Dec 22, 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
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Stevensville MD
Book a stay at this golf vacation home in Stevensville. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Matapeake State Park and Northern ...
9.8/10 Exceptional! (16 reviews)
This was our second time spending Thanksgiving week at Woodland Retreat. We appreciate the overall cleanliness of the house. All the beds are very comfortable. The kitchen is well stocked. The primary suite has plenty of room for baby’s portable crib. The downstairs bonus room is ideal for family ...
Reviewed on Nov 30, 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
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
- Annapolis Mall Shopping Center
- Chesapeake Bay Bridge
- Annapolis City Dock
- Anne Arundel Medical Center
- Sandy Point State Park
- Westfield Annapolis Mall
- Annapolis Harbor Center Shopping Center
- St. Michaels Winery
- Maryland State House
- Annapolis Maritime Museum
- Maryland Quiet Waters Park
- Rock Hall Harbor
- Queenstown Premium Outlets
- Avalon Theatre
- Maryland Hall for Creative Arts
- Chesapeake Bay Maritime Museum
- William Paca House
- Northern Chesapeake Bay
- Thurgood Marshall Memorial
- Queenstown Harbor Golf Club
