Sherwood, MD
Travel Guide
Visit Sherwood
Historic Inns of Annapolis
58 State Circle Annapolis MD
$159 nightly
The price is $181 total per night from May 31 to Jun 1
$181 total
May 31 - Jun 1
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)
"I wish there was a easier place to park, but it was a nice hotel"
Reviewed on May 19, 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
$98 nightly
The price is $111 total per night from May 24 to May 25
$111 total
May 24 - May 25
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! (1,003 reviews)
"hotel was clean and well appointed. The room was nice and comfortable. Breakfast buffet (continental) was just what I needed to start the day. And...the cookies were delicious."
Reviewed on May 20, 2026
Sonesta ES Suites Annapolis
170 Admiral Cochrane Dr Edgewater MD
$99 nightly
The price is $113 total per night from May 27 to May 28
$113 total
May 27 - May 28
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! (1,001 reviews)
"great"
Reviewed on May 20, 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! (244 reviews)
"We thoroughly enjoyed our stay! The Maghee House was bright, well appointed, up-to-date and very comfortable. We rented the home because it was on the water and had a nice dock to launch our kayaks. The area on Harris Creek was beautiful for kayaking. It would have been nice to have some empty cabinet ..."
Reviewed on May 12, 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
- Annapolis City Dock
- Chesapeake Bay
- Sandy Point State Park
- Chesapeake Bay Bridge
- Breezy Point Beach
- Blackwater National Wildlife Refuge
- Anne Arundel Medical Center
- Westfield Annapolis Mall
- Annapolis Mall Shopping Center
- Navy-Marine Corps Memorial Stadium
- Maryland State House
- Annapolis Harbor Center Shopping Center
- Chesapeake Bay Maritime Museum
- Queenstown Harbor Golf
- Northern Chesapeake Bay
- St. Michaels Winery
- Chesapeake Beach Water Park
- Harriet Tubman Underground Railroad National Historical Park
- Maryland Quiet Waters Park
- Gerry Boyle Park at Great Marsh
- William Paca House
- Rod n Reel Charter Fishing
- Annapolis Maritime Museum
- Choptank River Lighthouse