Sherwood, MD
Travel Guide
Visit Sherwood
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
$114 nightly
The price is $130 total per night from May 31 to Jun 1
$130 total
May 31 - Jun 1
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! (1,010 reviews)
It was the best hotel we have stayed in, in a very long time. Loved it!!!
Reviewed on May 10, 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
$163 nightly
The price is $186 total per night from May 25 to May 26
$186 total
May 25 - May 26
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! (1,854 reviews)
The only thing that was not 100% amazing was the toilet in our room was small and short and so was the shower head. I am only 5’4” so there is no way my husband would have been able to use either at 6’2”…. Other than that it was such an incredible historic place with all the grandeur and old wonderful ...
Reviewed on May 10, 2026
Sonesta ES Suites Annapolis
170 Admiral Cochrane Dr Edgewater MD
$108 nightly
The price is $123 total per night from May 26 to May 27
$123 total
May 26 - May 27
Total with taxes and fees
Book a stay at this business-friendly hotel in Parole. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,009 reviews)
It was very impressive...the room was perfect and the staff wa s super helpful and friendly
Reviewed on May 8, 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.
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! (53 reviews)
Absolutely Lovely, Julia was very sweet and the home had everything you could have thought of or forgotten to bring.
Reviewed on Apr 13, 2026
NEW! Charming Farm House in Historic Kent Island
Stevensville MD
Book a stay at this golf vacation home in Stevensville. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Chesapeake Bay Bridge and Paul ...
9/10 Wonderful! (16 reviews)
Comfy stay
comfortable for five and even the sixth person. Cute house, convenient location. Need instructions on using shower heads and on what tv channels are available.
Reviewed on Nov 3, 2022
Relaxing Waterfront Cottage Near St Michaels, Maryland
Wittman MD
Stay at this cottage in Wittman. Enjoy free WiFi, private pools, and laundry facilities. Our guests praise the property condition in our reviews. Popular attractions ...
9.8/10 Exceptional! (243 reviews)
Delightful, well-kept cottage.
Reviewed on May 1, 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.
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.
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- U.S. Naval Academy
- Chesapeake Bay
- Chesapeake Bay Bridge
- Annapolis City Dock
- Sandy Point State Park
- Annapolis Mall Shopping Center
- Westfield Annapolis Mall
- Breezy Point Beach
- Anne Arundel Medical Center
- Navy-Marine Corps Memorial Stadium
- Blackwater National Wildlife Refuge
- Northern Chesapeake Bay
- Maryland State House
- Chesapeake Bay Maritime Museum
- Annapolis Harbor Center Shopping Center
- Maryland Quiet Waters Park
- St. Michaels Winery
- Gerry Boyle Park at Great Marsh
- Harriet Tubman Underground Railroad National Historical Park
- Chesapeake Beach Water Park
- Annapolis Maritime Museum
- Queenstown Harbor Golf
- William Paca House
- Rod n Reel Charter Fishing
- Choptank River Lighthouse
- Queenstown Premium Outlets
