Sherwood, MD
Travel Guide
Visit Sherwood

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 ...
9/10 Wonderful! (1,822 reviews)
Nice stay
"We had a great room in the Governor Calvert House, very spacious with a big bathroom and comfortable bed. The amenities in the room were lacking however, there were two tiny water bottles and not enough coffee. Also, glass cups at the sink would be a lot nicer than the plastic ones they supplied. ..."
Reviewed on 14 September 2025

Sonesta ES Suites Annapolis
170 Admiral Cochrane Dr, Edgewater, MD
The price is SAR 388 per night from Sep 28 to Sep 29
SAR 388
SAR 443 total
28 Sep - 29 Sep
includes taxes & fees
Book a stay at this business-friendly hotel in Edgewater. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (886 reviews)
"Don't remember ever having to pay to park at a motel. Checking in was.a little rough but was a breeze checking out. The room appeared new, clean and quiet. Well thought out I mean, but for heaven's sake, stop charging people to park."
Reviewed on 15 September 2025

DoubleTree by Hilton Hotel Annapolis
210 Holiday Court, Annapolis, MD
The price is SAR 397 per night from Sep 29 to Sep 30
SAR 397
SAR 452 total
29 Sep - 30 Sep
includes taxes & fees
Stay at this 4-star business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ...
8.6/10 Excellent! (1,010 reviews)
Wonderful
"Truly exceptional stay. Service was extraordinary, conditions were very comfy...just a pleasure."
Reviewed on 13 September 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
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! (14 reviews)
"Incredible home & property. Spacious home with pool, hot tub, multiple large bedrooms, & room dedicated to crab eating! Property is massive & well maintained; golf cart & bikes made it very easy get around. The dock offers opportunities for boating, crabing, & fishing. Kayaks & canoe were great for ..."
Reviewed on 2 September 2025

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Sherwood
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! (34 reviews)
Sherwood Mansion
"We went to Sherwood to celebrate a family event. The house was perfect - lots of room for everyone. Check-in was simple, house was in excellent condition and the owners made every effort to accommodate our needs (some extra equipment for little kids). We enjoyed the pool and the beautiful setting. ..."
Reviewed on 6 August 2025

Cass-N-Reel Luxury Houseboat
Grasonville
Stay at this houseboat in Grasonville. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Chesapeake Bay Environmental Center and Paul ...
10/10 Exceptional! (38 reviews)
"Such a unique and lovely spot! Perfect for our weekend getaway. So many small touches that made us feel so welcomed. I didn’t pay attention to the pictures to notice it’s lifted out of the water, but with the wind & rain overnight we were thankful as we still heard the water lapping underneath but ..."
Reviewed on 10 September 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
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.
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.
- U.S. Naval Academy
- Chesapeake Bay Bridge
- Sandy Point State Park
- Annapolis City Dock
- Navy-Marine Corps Memorial Stadium
- Breezy Point Beach
- Blackwater National Wildlife Refuge
- Anne Arundel Medical Center
- Westfield Annapolis Mall
- Sandy Point Beach
- St. Michaels Winery
- Rod n Reel Charter Fishing
- Annapolis Harbor Center Shopping Center
- Chesapeake Beach Water Park
- Annapolis Maritime Museum
- Choptank River Lighthouse
- Maryland Quiet Waters Park
- Annapolis Mall Shopping Center
- Maryland State House
- Patuxent River
- Queenstown Premium Outlets
- Chesapeake Bay Maritime Museum
- Harriet Tubman Underground Railroad National Historical Park
- Long Wharf Park
- Annapolis Harbour Center
- Queenstown Harbor Golf Club
- London Town
- William Paca House
- Chesapeake Bay Environmental Center
