Chester, MD
Travel Guide
Visit Chester
Historic Inns of Annapolis
58 State Circle Annapolis MD
The price is AED 389 per night from Sep 27 to Sep 28
AED 389
AED 569 total
27 Sep - 28 Sep
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 ...
9/10 Wonderful! (1,982 reviews)
"Location, cleanliness, price, friendliness of the staff. Love it there. Only place we stay when visiting Annapolis."
Reviewed on 30 August 2026
Graduate by Hilton Annapolis
126 West St Annapolis MD
The price is AED 562 per night from Sep 13 to Sep 14
AED 562
AED 641 total
13 Sep - 14 Sep
includes taxes & fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and ...
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
The price is AED 358 per night from Sep 27 to Sep 28
AED 358
AED 409 total
27 Sep - 28 Sep
includes taxes & 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 ...
8.8/10 Excellent! (1,144 reviews)
"Clean room ,nice helpful staff and the shuttle service was 👍 great"
Reviewed on 31 August 2026
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.
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 Annapolis City ...
9.8/10 Exceptional! (52 reviews)
"Great spot for extended family to get together and very convenient to downtown Annapolis. Very cute neighborhood and kids could walk to the nearby shopping center for ice cream. Rooms are lovely - everything is new and nice."
Reviewed on 11 August 2026
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Rock Hall MD
Book a stay at this family-friendly villa in Rock Hall. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Rock Hall Harbor and The Mainstay ...
10/10 Exceptional! (48 reviews)
"This is a beautiful place! Spacious and very accommodating for large groups. We had 19 there and just tons of room. The grandkids loved the pool. The back yard faces the bay and provides a magnificant view for sunsets. Moreover, we were on the patio between the pool and breezeway when the feels like ..."
Reviewed on 8 August 2026
First Floor Studio Apartment in Historic Chestertown
Chestertown MD
Book a stay at this golf apartment in Chestertown. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Wilmer Park and Sumner Hall are ...
9.8/10 Exceptional! (124 reviews)
"Very nice, clean apartment in an excellent setting and location. It was perfect for our getaway to the eastern shore area. Certainly would recommend it and would stay there again."
Reviewed on 28 August 2026
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.
