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 ...
Historic Inns of Annapolis
58 State Circle Annapolis MD
$129 nightly
The price is $147 total per night from Aug 20 to Aug 21
$147 total
Aug 20 - Aug 21
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! (1,926 reviews)
"clean, extremely helpful staff, exactly as described"
Reviewed on Aug 5, 2026
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
$118 nightly
The price is $135 total per night from Aug 9 to Aug 10
$135 total
Aug 9 - Aug 10
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! (1,012 reviews)
"This was an amazing stay! My room got serviced daily while I was out exploring and they kept everything nice and clean! The breakfast add on was so worth it so if you have the option to definitely add it! I had an amazing time and can’t wait to stay again!"
Reviewed on Aug 3, 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! (18 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
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- Visit Stevensville
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- 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
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- Annapolis Maritime Museum
- Queenstown Harbor Golf
- Wye Landing
- Rock Hall Harbor
- Annapolis Landing Marina
- Chesapeake Bay Environmental Center
- Avalon Theatre
