Chester Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Patricia Knorr
Top hotels in Chester
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
The price is 3.071.023 ₫ per night from 31 May to 1 Jun
3.071.023 ₫
4.402.203 ₫ total
31 May - 1 Jun
includes taxes & fees
9/10 Wonderful! (1,851 reviews)
"Very helpful staff, nice ambiance"
Reviewed on 18 May 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
The price is 3.003.601 ₫ per night from 31 May to 1 Jun
3.003.601 ₫
3.424.105 ₫ total
31 May - 1 Jun
includes taxes & fees
Sonesta ES Suites Annapolis
170 Admiral Cochrane Dr Edgewater MD
Fully refundableReserve now, pay when you stay
The price is 2.608.848 ₫ per night from 27 May to 28 May
2.608.848 ₫
2.974.087 ₫ total
27 May - 28 May
includes taxes & fees
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.
