Visit Chester
Historic Inns of Annapolis
58 State Circle, Annapolis, MD
The price is $199 per night from May 6 to May 7
$199
includes taxes & fees
$145 per night
May 6 - May 7
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 ...
8.8/10 Excellent! (1,754 reviews)
"Great location and property!"
Reviewed on Apr 27, 2025
Country Inn & Suites by Radisson, Annapolis, MD
2600 Housley Road, Annapolis, MD
The price is $115 per night from May 6 to May 7
$115
includes taxes & fees
$101 per night
May 6 - May 7
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,008 reviews)
"I love the trees. I didn’t like the air wick plug in in my room though."
Reviewed on Apr 26, 2025
The Westin Annapolis
100 Westgate Cir, Annapolis, MD
The price is $170 per night from May 4 to May 5
$170
includes taxes & fees
$149 per night
May 4 - May 5
Stay at this 4-star spa hotel in Annapolis. Enjoy a full-service spa, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. ...
8.6/10 Excellent! (999 reviews)
"Hotel was under renovation so things were covered in plastic, etc. but overall very nice."
Reviewed on Apr 23, 2025
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.
Waterfront Sunset Bayview: sleeps 6
Chester
Stay at this vacation home in Chester. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Bodkin Island and Chesapeake Bay Environmental ...
10/10 Exceptional! (13 reviews)
Lovely clean home and nice yard.
"Really great spot, the house was very clean and new. We had nice weather and spent a lot of time outside and in the enclosed sun room."
Reviewed on Apr 20, 2025
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Annapolis
Book a stay at this family-friendly vacation home in Annapolis. Enjoy free WiFi, a water park, and patios. Popular attractions John Smith House and Annapolis ...
10/10 Exceptional! (194 reviews)
Wonderful location for walking everywhere
"Great location near the Naval Academy, Main Street, Paca House, St. John's...loved walking the streets every evening with our dog. Helpful restaurant trips from John, convenient parking spot, everything was just right! Thank you!"
Reviewed on Apr 26, 2025
The Blue Crab Beach House - Free beach passes
North Beach
Stay at this vacation home in North Beach. Enjoy free WiFi, a water park, and a garden. Popular attractions Bayside History Museum and Chesapeake Beach Water ...
10/10 Exceptional! (52 reviews)
You’ll be very happy!
"Cute as a button. Very, very clean, kitchen has everything, living room very comfortable for us 4 adults. Fenced yard was perfect for our furry companion. Excellent location-quiet neighborhood, easy walk to beach and restaurants.Host is very prompt responding to any inquiry. You won’t regret this ..."
Reviewed on Apr 15, 2025
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.
Popular places to visit
Chesapeake Exploration Center
Learn about the events happening at Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants.
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- Chesapeake Exploration Center
- U.S. Naval Academy
- Chesapeake Bay Bridge
- Annapolis City Dock
- Sandy Point State Park
- Navy-Marine Corps Memorial Stadium
- Westfield Annapolis Mall
- Anne Arundel Medical Center
- St. Michaels Winery
- Rock Hall Harbor
- Maryland Quiet Waters Park
- Annapolis Harbour Center
- Annapolis Maritime Museum
- Annapolis Harbor Center Shopping Center
- Queenstown Premium Outlets
- Annapolis Mall Shopping Center
- Chesapeake Bay Maritime Museum
- Maryland State House
- William Paca House
- Queenstown Harbor Golf Club
- U.S. Naval Academy Golf Club
- Thurgood Marshall Memorial
- Avalon Theatre
- Chesapeake Bay Environmental Center
- Maryland Hall for Creative Arts
- Annapolis Landing Marina
- Eastern Neck National Wildlife Refuge
- Fort Smallwood Park