Visit Chester
Historic Inns of Annapolis
58 State Circle, Annapolis, MD
The price is AU$267 per night from 5 Nov to 6 Nov
AU$267
5 Nov - 6 Nov
includes taxes & 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! (1,863 reviews)
"So the entire experience was amazing. There was so much in walking distance. It was kind of weird because there were actually 3 inns and we didn't know which one we were in"
Reviewed on 28 Sept 2025
Sonesta ES Suites Annapolis
170 Admiral Cochrane Dr, Edgewater, MD
The price is AU$180 per night from 2 Nov to 3 Nov
AU$180
2 Nov - 3 Nov
includes taxes & fees
Book a stay at this business-friendly hotel in Parole. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (903 reviews)
"Overall, the property was clean and maintained. The rooms were clean, but a bit tired. Staff was very nice and accommodating."
Reviewed on 30 Sept 2025
Country Inn & Suites by Radisson, Annapolis, MD
2600 Housley Road, Annapolis, MD
The price is AU$167 per night from 2 Nov to 3 Nov
AU$167
2 Nov - 3 Nov
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 ...
8.8/10 Excellent! (1,000 reviews)
"This was a convenient property for visiting the Naval Academy and historic Annapolis. The property seemed to be well taken care of. The breakfast was the usual breakfast area with a waffle maker, oatmeal, a hot serving dish of an egg product, a meat, and a potato product. Nothing fancy. The room ..."
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! (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 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! (117 reviews)
"Beautifully restored historic home, in a quaint neighborhood, near the water and downtown. We loved it!"
Reviewed on 21 Sept 2025
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Annapolis
Stay at this vacation home in Annapolis. Enjoy free WiFi, a water park, and laundry facilities. Popular attractions John Smith House and Tose Family Tennis Center ...
10/10 Exceptional! (215 reviews)
"Perfect location and lovely place for a weekend getaway!"
Reviewed on 14 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.
