Chester
Travel Guide
Visit Chester
Historic Inns of Annapolis
58 State Circle Annapolis MD
The price is CA $147 per night from Sep 29 to Sep 30
CA $147
CA $215 total
Sep 29 - Sep 30
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! (1,981 reviews)
"I like the Maryland House. Great porch. Excellent location."
Reviewed on Aug 30, 2026
Graduate by Hilton Annapolis
126 West St Annapolis MD
The price is CA $213 per night from Sep 13 to Sep 14
CA $213
CA $243 total
Sep 13 - Sep 14
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 CA $136 per night from Sep 27 to Sep 28
CA $136
CA $155 total
Sep 27 - Sep 28
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 ...
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 Aug 11, 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 Aug 8, 2026
Waterfront Oasis of Annapolis Star
Annapolis MD
Stay at this apartment in Annapolis. Enjoy free WiFi, private pools, and a garden. Popular attractions Annapolis City Dock and Sandy Point State Park are located ...
10/10 Exceptional! (87 reviews)
"Couldn’t recommend any more. Beth & Andy are great hosts."
Reviewed on Aug 2, 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
CA $339
per adult
St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty
CA $220
per adult
2-Hour Relaxing Chesapeake Day Sail on Lady Patty
CA $221
per adult
