Visit Chester
Historic Inns of Annapolis
58 State Circle, Annapolis, MD
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! (1,841 reviews)
"Nice and clean room in historical building. Next to state building in historic district of the town"
Reviewed on 22 Sept 2025
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court, Annapolis, MD
The price is €103 per night from 29 Sept to 30 Sept
€103
29 Sept - 30 Sept
includes taxes & fees
Stay at this 4-star business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ...
8.6/10 Excellent! (1,015 reviews)
McMullen Symposium
"Clean room, efficient staff and superb breakfast. Grateful thanks to the hotel staff."
Reviewed on 21 Sept 2025
Country Inn & Suites by Radisson, Annapolis, MD
2600 Housley Road, Annapolis, MD
The price is €98 per night from 6 Oct to 7 Oct
€98
6 Oct - 7 Oct
includes taxes & 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 ...
9/10 Wonderful! (1,019 reviews)
"We booked a pet friendly suite. Over all the room wasn’t too bad, a little smaller than we expected considering he was a suite. The staff was great. The buffet was also great. The ‘grassy area’ left a bit to be desired although there was grass ina nd around d the hotel. It"
Reviewed on 22 Sept 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 Matapeake State Park and ...
9.8/10 Exceptional! (93 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 14 Sept 2025
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Saint Michaels
Stay at this cottage in St. Michaels. Enjoy a garden, laundry facilities, and tennis courts. Popular attractions Muskrat Park and Higgins Yacht Yard and Marina ...
9.4/10 Exceptional! (116 reviews)
"Beautifully restored historic home, in a quaint neighborhood, near the water and downtown. We loved it!"
Reviewed on 21 Sept 2025
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Annapolis
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! (35 reviews)
"Beautiful view, great property. Owner was easy to communicate with"
Reviewed on 1 Sept 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 in Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants.
