Chester Holidays
Photo by Patricia Knorr
- Plan, book, travel with confidence
- Better togetherSave up to €185 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Chester
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Chester MD
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
Sonesta ES Suites Annapolis
170 Admiral Cochrane Dr Edgewater MD
Fully refundableReserve now, pay when you stay
The price is €87 per night from 8 Mar to 9 Mar
€87
8 Mar - 9 Mar
includes taxes & fees
8.8/10 Excellent! (988 reviews)
Great place. Perfect.
Reviewed on 11 Feb 2026
Graduate by Hilton Annapolis
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
The price is €156 per night from 1 Mar to 2 Mar
€156
1 Mar - 2 Mar
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
Clean comfortable room!
Reviewed on 8 Feb 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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
