Chester, MD

Travel Guide

Photo by Patricia Knorr
Photo by Patricia Knorr
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
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! (1,835 reviews)
"Beautiful hotel in the heart of Annapolis. Lots of charm"

Reviewed on 3 October 2025

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Historic Inns of Annapolis
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3 out of 5
170 Admiral Cochrane Dr, Edgewater, MD
The price is AED 380 per night from Nov 2 to Nov 3
AED 380
AED 434 total
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 September 2025

Sonesta ES Suites Annapolis
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3 out of 5
2600 Housley Road, Annapolis, MD
The price is AED 356 per night from Nov 2 to Nov 3
AED 356
AED 406 total
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! (1,004 reviews)
"Great place to stay Friendly staff secure rooms Thank you"

Reviewed on 2 October 2025

Country Inn & Suites by Radisson, Annapolis, MD
See all 1,254 properties in Chester
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!

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 September 2025

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

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 September 2025

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

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! (36 reviews)
"Beautiful view, great property. Owner was easy to communicate with"

Reviewed on 1 September 2025

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
See all properties in Chester
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.

Chesapeake Exploration Center