Sherwood, MD
Travel Guide
Visit Sherwood
Historic Inns of Annapolis
58 State Circle, Annapolis, MD
$143 nightly
The price is $163 total per night from Jul 21 to Jul 22
$163 total
Jul 21 - Jul 22
Total includes 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 ...
8.8/10 Excellent! (1,805 reviews)
"We love our stay here for our son’s USNA I Day."
Reviewed on Jul 13, 2025
Graduate by Hilton Annapolis
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $177 total per night from Aug 3 to Aug 4
$177 total
Aug 3 - Aug 4
Total includes taxes and fees
Stay at this 4-star business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and ...
9.4/10 Exceptional! (1,011 reviews)
Convenient
"Conveniently located to many restaurants and shops. Easy walk to Rams Head venue."
Reviewed on Jul 12, 2025
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court, Annapolis, MD
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $118 total per night from Aug 3 to Aug 4
$118 total
Aug 3 - Aug 4
Total includes taxes and fees
Stay at this 4-star business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ...
8.4/10 Very Good! (1,002 reviews)
"Staff was very nice and professional!"
Reviewed on Jul 10, 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.
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Sherwood
Book a stay at this family-friendly vacation home in Sherwood. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Goat Island and Back ...
10/10 Exceptional! (33 reviews)
Beautiful home and tons of space
"This is a beautiful property, well appointed, but not too formal for families wanting to be in the pool or on the water all day. We were a party of 12 including six grandchildren. There was plenty to do for the adults and the grandchildren and plenty of space in the home to not feel like you were ..."
Reviewed on Jul 9, 2025
Waterfront Oasis of Annapolis Star
Annapolis
Stay at this apartment in Annapolis. Enjoy free WiFi, private pools, and a water park. Popular attractions Annapolis City Dock and U.S. Naval Academy Golf Club ...
10/10 Exceptional! (73 reviews)
Beautiful Place
"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."
Reviewed on Feb 19, 2025
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Annapolis
Stay at this vacation home in Annapolis. Enjoy free WiFi, a water park, and laundry facilities. Popular attractions Annapolis City Dock and John Smith House ...
10/10 Exceptional! (208 reviews)
Phenomenal Stay in Annapolis!
"This wonderful home is cozy and inviting! Unbeatable location and very accommodating in so many ways! John was an excellent host - 5 Stars!"
Reviewed on Jul 10, 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
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.
Explore a world of travel with Expedia
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- U.S. Naval Academy
- Annapolis City Dock
- Chesapeake Bay Bridge
- Sandy Point State Park
- Navy-Marine Corps Memorial Stadium
- Breezy Point Beach
- Anne Arundel Medical Center
- Westfield Annapolis Mall
- Blackwater National Wildlife Refuge
- St. Michaels Winery
- Chesapeake Beach Water Park
- Rod n Reel Charter Fishing
- Annapolis Harbor Center Shopping Center
- Annapolis Mall Shopping Center
- Maryland Quiet Waters Park
- Annapolis Maritime Museum
- Choptank River Lighthouse
- Queenstown Premium Outlets
- Maryland State House
- Chesapeake Bay Maritime Museum
- Harriet Tubman Underground Railroad National Historical Park
- William Paca House
- Annapolis Harbour Center
- Queenstown Harbor Golf Club
- Long Wharf Park
- Gerry Boyle Park at Great Marsh