Chester
Travel Guide
Visit Chester
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
The price is HK$830 per night from 29 Sept to 30 Sept
HK$830
HK$1,214 total
29 Sept - 30 Sept
includes taxes & fees
Stay at this historic hotel in Annapolis. Enjoy free Wi-Fi, room service and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,976 reviews)
"The locations were confusing but the property we stayed at was decorated gorgeous."
Reviewed on 30 Aug 2026
Graduate by Hilton Annapolis
126 West St Annapolis MD
The price is HK$1,200 per night from 13 Sept to 14 Sept
HK$1,200
HK$1,369 total
13 Sept - 14 Sept
includes taxes & fees
Stay at this business-friendly hotel in Annapolis. Enjoy free Wi-Fi, breakfast (surcharge) and a 24-hour fitness centre. Our guests praise the bar and the helpful ...
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
The price is HK$765 per night from 27 Sept to 28 Sept
HK$765
HK$872 total
27 Sept - 28 Sept
includes taxes & fees
Stay at this business-friendly hotel in Annapolis. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the restaurant and the helpful ...
8.8/10 Excellent! (1,136 reviews)
"Shower was clogged water backing up while taking shower. Pool was supposed to be open till 9pm but life guard left early and pool was closed with gate locked by 8pm. Didn't get informed of that at check in."
Reviewed on 30 Aug 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 holiday home in Annapolis. Enjoy a fitness centre, 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 Aug 2026
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Rock Hall MD
Stay at this family-friendly villa in Rock Hall. Enjoy free Wi-Fi, private pools and a fitness centre. 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 Aug 2026
First Floor Studio Apartment in Historic Chestertown
Chestertown MD
Stay at this golf apartment in Chestertown. Enjoy free Wi-Fi, private pools and a fitness centre. Popular attractions Wilmer Park and Sumner Hall are located ...
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 Aug 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.
Stay near popular Chester attractions
Things to do
2 Hour Chesapeake Day Sail on Catamaran Epiphany
HK$1,921
per adult
St. Michaels: 2-Hour Relaxing Chesapeake Sail on Epiphany
HK$2,117
per adult
2-Hour Relaxing Chesapeake Day Sail on Lady Patty
HK$1,255
per adult
