Sherwood, MD
Travel Guide
Visit Sherwood
Historic Inns of Annapolis
58 State Circle Annapolis MD
$146 nightly
The price is $166 total per night from Jun 16 to Jun 17
$166 total
Jun 16 - Jun 17
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! (1,871 reviews)
"Excellent location, walking distance to everything we had plans on seeing"
Reviewed on Jun 9, 2026
Hyatt Regency Chesapeake Bay
100 Heron Blvd Cambridge MD
$316 nightly
The price is $359 total per night from Jun 10 to Jun 11
$359 total
Jun 10 - Jun 11
Total with taxes and fees
Book a stay at this beach resort in Cambridge. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
8.8/10 Excellent! (1,007 reviews)
"The hotel was very nice enjoyed my stay."
Reviewed on Jun 8, 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
$104 nightly
The price is $119 total per night from Jun 10 to Jun 11
$119 total
Jun 10 - Jun 11
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! (1,015 reviews)
"The bed and sheets were very comfortable for quality sleeping. Nice towels as well. Air conditioning was loud. The attached restaurant had wonderful food. The pool was great, even a lifeguard on duty! The traffic unfortunately is loud from the highway."
Reviewed on Jun 9, 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.
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Annapolis MD
Stay at this vacation home in Annapolis. Enjoy free WiFi, laundry facilities, and patios. Popular attractions John Smith House and Tose Family Tennis Center ...
10/10 Exceptional! (248 reviews)
"The house is in a great location. It is very historic and the inside is quaint as you would expect in a historic house. The single garage is around the corner and a tight squeeze. You have to either double park in front to unload (not ideal on a busy street corner) or unload at the garage and walk ..."
Reviewed on Jun 9, 2026
Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock
Bozman MD
Stay at this cottage in Bozman. Enjoy air conditioning. Popular attractions Neavitt Park and Back Creek Park are located nearby.
Private Pool & Stunning Bay Views on Kent Island
Stevensville MD
Stay at this vacation home in Stevensville. Enjoy free WiFi, private pools, and a garden. Popular attractions Matapeake State Park and Romancoke Wharf County ...
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
- Sandy Point State Park
- Annapolis City Dock
- Chesapeake Bay Bridge
- Anne Arundel Medical Center
- Breezy Point Beach
- Westfield Annapolis Mall
- Blackwater National Wildlife Refuge
- Maryland State House
- Navy-Marine Corps Memorial Stadium
- Annapolis Mall Shopping Center
- Queenstown Harbor Golf
- Gerry Boyle Park at Great Marsh
- Chesapeake Bay Environmental Center
- Chesapeake Bay Maritime Museum
- Annapolis Harbor Center Shopping Center
- St. Michaels Winery
- Northern Chesapeake Bay
- Queenstown Premium Outlets
- Avalon Theatre
- Chesapeake Beach Water Park
- Maryland Quiet Waters Park
- Rod n Reel Charter Fishing
