Sherwood, MD
Travel Guide
Visit Sherwood
Historic Inns of Annapolis
58 State Circle Annapolis MD
$145 nightly
The price is $165 total per night from Jun 15 to Jun 16
$165 total
Jun 15 - Jun 16
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! (1,863 reviews)
"Hotel was very nice. Staff were helpful and very clean"
Reviewed on Jun 6, 2026
Annapolis Waterfront Hotel, Autograph Collection
80 Compromise St Annapolis MD
$212 nightly
The price is $241 total per night from Jun 14 to Jun 15
$241 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! (936 reviews)
"Definitely the view of the harbor from our room and how all the stores and restaurants were in walking distance"
Reviewed on Jun 5, 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
$95 nightly
The price is $109 total per night from Jun 7 to Jun 8
$109 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! (1,011 reviews)
"Small old rooms. Old architecture. Lots of maintenance needed in room, etc. Hotel is only 2.5 stars not 4!"
Reviewed on Jun 5, 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
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Annapolis MD
Stay at this vacation home in Annapolis. Enjoy free WiFi, laundry facilities, and patios. Popular attractions John Smith House and Tose Family Tennis Center ...
10/10 Exceptional! (247 reviews)
"John (owner) was amazing! Quick response, provided excellent information!"
Reviewed on May 31, 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
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