Sherwood, MD
Travel Guide
Visit Sherwood
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
$83 nightly
The price is $94 total per night from Jan 4 to Jan 5
$94 total
Jan 4 - Jan 5, 2026
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)
Great place!
Reviewed on Dec 3, 2025
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $164 total per night from Jan 1 to Jan 2
$164 total
Jan 1 - Jan 2, 2026
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 ...
8.8/10 Excellent! (1,898 reviews)
Rooms are in the different buildings so we needed to check in to find out where we were staying. Parking is difficult so we chose to pay for valet. Loved the location and it was convenient for Midnight Madness shopping and to great restaurants.
Reviewed on Dec 6, 2025
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
$97 nightly
The price is $111 total per night from Dec 15 to Dec 16
$111 total
Dec 15 - Dec 16
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 helpful staff and the ...
8.6/10 Excellent! (1,017 reviews)
Mold on the fruit at Breakfast. Grapefruit dried out. Broken bathroom fixtures (toilet paper holder & magnifying mirror). No extra blanket in closet since husband and I like to sleep at different temperature. Moldy grout in bathroom.
Reviewed on Dec 2, 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.
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! (20 reviews)
This place is spacious, comfortable, and so clean. Well-maintained outdoor grounds, very nice and helpful caretaker, amazing to have access to boats/life jackets, golf cart, and fire pit!
Reviewed on Nov 19, 2025
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
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
- Navy-Marine Corps Memorial Stadium
- Chesapeake Bay
- Annapolis City Dock
- Chesapeake Bay Bridge
- Anne Arundel Medical Center
- Annapolis Mall Shopping Center
- Sandy Point State Park
- Westfield Annapolis Mall
- Blackwater National Wildlife Refuge
- Annapolis Harbor Center Shopping Center
- Maryland State House
- Breezy Point Beach
- Maryland Quiet Waters Park
- Harriet Tubman Underground Railroad National Historical Park
- Annapolis Maritime Museum
- Queenstown Premium Outlets
- St. Michaels Winery
- Rod n Reel Charter Fishing
- Gerry Boyle Park at Great Marsh
- Maryland Hall for Creative Arts
- Choptank River Lighthouse
- Chesapeake Bay Maritime Museum
- Avalon Theatre
- William Paca House
- Chesapeake Beach Water Park
- Northern Chesapeake Bay
