Chester, MD
Travel Guide
Visit Chester
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
$98 nightly
The price is $111 total per night from Aug 30 to Aug 31
$111 total
Aug 30 - Aug 31
Total with taxes and 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! (1,090 reviews)
"Property was clean but a bit dated , staff was exceptional, AC was loud"
Reviewed on Aug 9, 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $150 total per night from Aug 17 to Aug 18
$150 total
Aug 17 - Aug 18
Total with taxes and 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! (1,938 reviews)
"This weekend’s stay at Historic Inn of Annapolis was amazing. From the check in to the valet staff to the late check out was awesome! The family loved it and it was super close to the Naval academy which is what we were there for. The history surrounding the hotel was just astonishing. I highly recommend ..."
Reviewed on Aug 9, 2026
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
$110 nightly
The price is $125 total per night from Sep 1 to Sep 2
$125 total
Sep 1 - Sep 2
Total with taxes and fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.8/10 Excellent! (1,017 reviews)
"As someone allergic to feathers/down in pillows and blankets, I was happy to hear they no longer carry these items. I do not like that the hotel charges more for an allergen treated room. Shouldn't all rooms be allergy free? The restaurant needs more help and posted hours. One person running breakfast ..."
Reviewed on Aug 10, 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.
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Annapolis MD
Stay at this vacation home in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a garden. Popular attractions Annapolis City Dock and Bay Ridge Beach are ...
Cute, Cozy 2-bedroom house near Annapolis with water access
Crownsville MD
Stay at this vacation home in Crownsville. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Joyces Marina and B&A Trail are located ...
9.6/10 Exceptional! (19 reviews)
"Great stay"
Reviewed on Aug 2, 2026
Waterfront Oasis of Annapolis Star
Annapolis MD
Stay at this apartment in Annapolis. Enjoy free WiFi, private pools, and cable/satellite TV service. Popular attractions Annapolis City Dock and Sandy Point ...
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
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- Visit Arnold
- Visit Historic District
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- Visit Stevensville
- Visit Wittman
- Visit Wye Mills
- Chesapeake Exploration Center
- U.S. Naval Academy
- Sandy Point State Park
- Annapolis City Dock
- Chesapeake Bay
- Chesapeake Bay Bridge
- Navy-Marine Corps Memorial Stadium
- Maryland State House
- Westfield Annapolis Mall
- Anne Arundel Medical Center
- St. Michaels Winery
- Northern Chesapeake Bay
- William Paca House
- Chesapeake Bay Maritime Museum
- Annapolis Mall Shopping Center
- Maryland Quiet Waters Park
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- Annapolis Harbour Center
- Annapolis Maritime Museum
- Queenstown Harbor Golf
- Wye Landing
- Rock Hall Harbor
- Annapolis Landing Marina
- Chesapeake Bay Environmental Center
- Avalon Theatre
