Sherwood, MD
Travel Guide
Visit Sherwood

Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
The price is AED 394 per night from Nov 30 to Dec 1
AED 394
AED 449 total
30 Nov - 1 Dec
includes taxes & 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! (1,008 reviews)
No hot shower in Suite for three days
Reviewed on 19 November 2025

Historic Inns of Annapolis
58 State Circle Annapolis MD
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! (1,902 reviews)
Location perfect
Reviewed on 23 November 2025

DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
The price is AED 222 per night from Dec 21 to Dec 22
AED 222
AED 253 total
21 Dec - 22 Dec
includes taxes & 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! (1,027 reviews)
Clean, friendly staff. Restaurant/ bar food was excellent and staff in the restaurant/ bar were fun and accommodating!
Reviewed on 26 November 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 ...
9.8/10 Exceptional! (19 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 19 November 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 20 October 2025

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Annapolis MD
Stay at this vacation home in Annapolis. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions Ellen O. Moyer Nature Park at Back ...
10/10 Exceptional! (32 reviews)
Excellent location and large house! Would love to stay again.
Reviewed on 16 November 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.
- 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
- Sandy Point Beach
- Breezy Point Beach
- Maryland State House
- Maryland Quiet Waters Park
- Harriet Tubman Underground Railroad National Historical Park
- St. Michaels Winery
- Queenstown Premium Outlets
- Annapolis Maritime Museum
- Maryland Hall for Creative Arts
- Gerry Boyle Park at Great Marsh
- Choptank River Lighthouse
- Rod n Reel Charter Fishing
- William Paca House
- Avalon Theatre
- Chesapeake Bay Maritime Museum
- Patuxent River
- Chesapeake Beach Water Park
- Northern Chesapeake Bay
