Sherwood, MD
Travel Guide
Visit Sherwood
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
$146 nightly
The price is $166 total per night from Jun 16 to Jun 17
$166 total
Jun 16 - Jun 17
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! (1,858 reviews)
"Lovely hotel. Clean rooms, friendly staff. Highly recommend"
Reviewed on Jun 2, 2026
Annapolis Waterfront Hotel, Autograph Collection
80 Compromise St Annapolis MD
$220 nightly
The price is $251 total per night from Jun 14 to Jun 15
$251 total
Jun 14 - Jun 15
Total with taxes and fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff ...
8.8/10 Excellent! (935 reviews)
"The room was incredibly small."
Reviewed on Jun 2, 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
$100 nightly
The price is $114 total per night from Jun 7 to Jun 8
$114 total
Jun 7 - Jun 8
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! (1,008 reviews)
"It would have been a nicer stay if they weren’t ripping up flooring and had the awful headache causing smell of epoxy everywhere. The hotel room we were in was in another wing- and you had to pass all around the convention rooms to get there. Thankfully we were able to use the shuttle to go into ..."
Reviewed on Jun 2, 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.
Lovely bay views with kayaks, bikes, fire pit, crabbing & more
Shady Side MD
Book a stay at this family-friendly vacation home in Shady Side. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Shadyside Park and Captain ...
9.8/10 Exceptional! (31 reviews)
"Bright clean beach house in a nice family-friendly and pet-friendly neighborhood. We really appreciated the large fenced-in backyard and being supplied with bottled water and the thoughtful dog basket. The beach house was perfect for two couples. The driving distance between the house and dining ..."
Reviewed on Jun 2, 2026
Charming Annapolis WaterVIEW Home
Annapolis MD
Stay at this vacation home in Annapolis. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Bay Ridge Beach and Annapolis Golf Club are located ...
9.8/10 Exceptional! (70 reviews)
"Our family had a wonderful stay at your beautiful home! The views are to die for! House was very clean with all equipment and kitchen appliances all available! Very happy with our stay!"
Reviewed on May 3, 2026
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 ...
9.8/10 Exceptional! (57 reviews)
"Such a cool experience"
Reviewed on May 24, 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
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
- Chesapeake Bay
- Annapolis City Dock
- Chesapeake Bay Bridge
- Westfield Annapolis Mall
- Sandy Point State Park
- Breezy Point Beach
- Anne Arundel Medical Center
- Blackwater National Wildlife Refuge
- Maryland State House
- Navy-Marine Corps Memorial Stadium
- Gerry Boyle Park at Great Marsh
- Annapolis Mall Shopping Center
- Queenstown Harbor Golf
- Annapolis Harbor Center Shopping Center
- Chesapeake Bay Maritime Museum
- Northern Chesapeake Bay
- Maryland Quiet Waters Park
- Chesapeake Bay Environmental Center
- Annapolis Maritime Museum
- Harriet Tubman Underground Railroad National Historical Park
- St. Michaels Winery
- Avalon Theatre
- Chesapeake Beach Water Park
- Rod n Reel Charter Fishing