Sherwood, MD
Travel Guide
Visit Sherwood
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Sherwood MD
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! (37 reviews)
What a spectacular home!! We all loved our stay and took advantage of the beautiful heated pool, dock, fire pit and playground. In the evening the pool table, ping pong and foosball were enjoyed by all. Stunning views, beautiful furnishings and comfortable bedding. Hopefully we will have occasion ...
Reviewed on Oct 20, 2025
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
$75 nightly
The price is $86 total per night from Feb 8 to Feb 9
$86 total
Feb 8 - Feb 9
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! (1,000 reviews)
Staff was amazing!!! The place was clean!!! Bathroom was out dated and had a couple holes in the ceiling by the fan. Pillows were tiny, that was probably my biggest issue. Had a restaurant inside, didn’t stop in during the evening. Had breakfast, price was reasonable. Got the buffet, food was ...
Reviewed on Jan 6, 2026
Graduate by Hilton Annapolis
126 West St Annapolis MD
$147 nightly
The price is $167 total per night from Jan 18 to Jan 19
$167 total
Jan 18 - Jan 19
Total with taxes and fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and ...
9.2/10 Wonderful! (1,004 reviews)
Pleasant staff. Good location to walk to restaurants, shops.
Reviewed on Dec 30, 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 MD
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! (37 reviews)
What a spectacular home!! We all loved our stay and took advantage of the beautiful heated pool, dock, fire pit and playground. In the evening the pool table, ping pong and foosball were enjoyed by all. Stunning views, beautiful furnishings and comfortable bedding. Hopefully we will have occasion ...
Reviewed on Oct 20, 2025
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
Sherwood MD
Book a stay at this family-friendly vacation home in Sherwood. Enjoy private pools, a private beach, and a garden. Popular attractions Back Creek Community Park ...
10/10 Exceptional! (21 reviews)
Wonderful for our needs this Thanksgiving. Playroom was full of blocks, books and puzzles. Hot tub was the best!! Kitchen is so well stocked!
Reviewed on Nov 30, 2025
Floating 2 bed 2 bath condo stunning views of the bay
Stevensville MD
Stay at this houseboat in Stevensville. Enjoy a beach locale and an in-room coffeemaker. Popular attractions Matapeake State Park and Romancoke Wharf County ...
7/10 Good! (6 reviews)
Husband & I stayed during the Annapolis boat show to get a feel for what living on a yacht would be like for our year Great Loop adventure and to see what boat features would be important to us when buying. This stay suited us perfectly and Kate’s communication with us with very quick. A minor mechanical ...
Reviewed on Oct 8, 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.
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- U.S. Naval Academy
- Anne Arundel Medical Center
- Chesapeake Bay Bridge
- Annapolis City Dock
- Annapolis Mall Shopping Center
- Navy-Marine Corps Memorial Stadium
- Sandy Point State Park
- Chesapeake Bay
- Blackwater National Wildlife Refuge
- Westfield Annapolis Mall
- Breezy Point Beach
- Annapolis Maritime Museum
- St. Michaels Winery
- Annapolis Harbor Center Shopping Center
- Harriet Tubman Underground Railroad National Historical Park
- Maryland State House
- Maryland Quiet Waters Park
- Queenstown Premium Outlets
- Choptank River Lighthouse
- Gerry Boyle Park at Great Marsh
- Chesapeake Bay Maritime Museum
- Chesapeake Beach Water Park
- Maryland Hall for Creative Arts
- Dorchester County Visitors Center
- Avalon Theatre
- Harriet Tubman Museum and Educational Center
