Sherwood, MD
Travel Guide
Visit Sherwood
Historic Inns of Annapolis
58 State Circle Annapolis MD
$159 nightly
The price is $181 total per night from Jun 8 to Jun 9
$181 total
Jun 8 - Jun 9
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! (1,854 reviews)
"Great location with views all the way to the Bay Bridge from some rooms. Comfortable and spacious room."
Reviewed on May 30, 2026
Annapolis Waterfront Hotel, Autograph Collection
80 Compromise St Annapolis MD
$220 nightly
The price is $251 total per night from Jun 7 to Jun 8
$251 total
Jun 7 - Jun 8
Total with taxes and fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff ...
8.8/10 Excellent! (931 reviews)
"Valet was full had to park garage pretty far away as well as a poor check in experience"
Reviewed on May 29, 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
$102 nightly
The price is $116 total per night from Jun 7 to Jun 8
$116 total
Jun 7 - Jun 8
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 ...
8.6/10 Excellent! (1,004 reviews)
"Very dated rooms with signs of wear and tear. They are in the act of some redos. Lobby area and bar nice."
Reviewed on May 30, 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.
Lovely bay views with kayaks, bikes, fire pit, crabbing & more
Shady Side MD
Book a stay at this family-friendly vacation home in Shady Side. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Shadyside Park and Captain ...
9.8/10 Exceptional! (29 reviews)
"Very clean with modern decor. Owners were attentive and gave detailed instructions for check-in and check-out. Plenty of beds and extra sheets, blankets and towels. Large dining table for game nights. Additional game shed/man cave in the back yard. Very nice property in a cute area with views of ..."
Reviewed on Apr 3, 2026
Charming Annapolis WaterVIEW Home
Annapolis MD
Stay at this vacation home in Annapolis. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Bay Ridge Beach and Annapolis Golf Club are located ...
9.8/10 Exceptional! (70 reviews)
"Our family had a wonderful stay at your beautiful home! The views are to die for! House was very clean with all equipment and kitchen appliances all available! Very happy with our stay!"
Reviewed on May 3, 2026
Chesapeake Houseboat Getaway on Kent Island, Maryland
Stevensville MD
Stay at this houseboat in Stevensville. Enjoy patios, an in-room coffeemaker, and in-room fireplaces. Popular attractions Romancoke Wharf County Park and Matapeake ...
9.8/10 Exceptional! (57 reviews)
"Such a cool experience"
Reviewed on May 24, 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.
Popular places to visit
Back Creek Community Park
Back Creek Community Park is just one of the places to see in Sherwood, so why not enjoy the other things to explore during your travels? Wander the marina or discover the area's sunsets.
Goat Island
Commune with nature and explore the great outdoors at Goat Island during your travels in Sherwood. Wander the marina or discover the area's sunsets.
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- U.S. Naval Academy
- Chesapeake Bay
- Annapolis City Dock
- Chesapeake Bay Bridge
- Sandy Point State Park
- Breezy Point Beach
- Westfield Annapolis Mall
- Anne Arundel Medical Center
- Blackwater National Wildlife Refuge
- Maryland State House
- Chesapeake Bay Maritime Museum
- Navy-Marine Corps Memorial Stadium
- Gerry Boyle Park at Great Marsh
- Annapolis Mall Shopping Center
- Annapolis Harbor Center Shopping Center
- Chesapeake Bay Environmental Center
- Northern Chesapeake Bay
- Queenstown Harbor Golf
- Harriet Tubman Underground Railroad National Historical Park
- Avalon Theatre
- Chesapeake Beach Water Park
- Harriet Tubman Museum and Educational Center
- William Paca House
- Rod n Reel Charter Fishing
- Choptank River Lighthouse
