Sherwood, MD
Travel Guide
Visit Sherwood
Historic Inns of Annapolis
58 State Circle Annapolis MD
$130 nightly
The price is $148 total per night from Jul 5 to Jul 6
$148 total
Jul 5 - Jul 6
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! (1,886 reviews)
"I would’ve liked to have the ability to access Netflix."
Reviewed on Jun 14, 2026
Hyatt Regency Chesapeake Bay
100 Heron Blvd Cambridge MD
$307 nightly
The price is $348 total per night from Jun 16 to Jun 17
$348 total
Jun 16 - Jun 17
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! (1,008 reviews)
"The hotel was very nice enjoyed my stay."
Reviewed on Jun 8, 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
$111 nightly
The price is $127 total per night from Jun 16 to Jun 17
$127 total
Jun 16 - Jun 17
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! (1,022 reviews)
"Loved the shuttle that could take you within 5 Mi of the place. It really helped us to get around in a town with limited parking"
Reviewed on Jun 14, 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! (246 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
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 ...
10/10 Exceptional! (57 reviews)
"I have stayed at many places over the years. This would be my favorite place. The view and the location was unbelievable. We were in town for a wedding and our host let us check in early to accommodate the wedding schedule. I would definitely recommend this house boat to anyone that wants a unique ..."
Reviewed on Jun 1, 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.
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 Sherwood attractions
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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
- Gerry Boyle Park at Great Marsh
- Navy-Marine Corps Memorial Stadium
- Annapolis Mall Shopping Center
- Queenstown Harbor Golf
- Chesapeake Bay Environmental Center
- Chesapeake Bay Maritime Museum
- Annapolis Harbor Center Shopping Center
- St. Michaels Winery
- Queenstown Premium Outlets
- Maryland Quiet Waters Park
- Northern Chesapeake Bay
- Avalon Theatre
- Chesapeake Beach Water Park
- Thanksgiving Farm Wines
- Rod n Reel Charter Fishing
