Sherwood, MD
Travel Guide
Visit Sherwood
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
$95 nightly
The price is $109 total per night from Jul 5 to Jul 6
$109 total
Jul 5 - Jul 6
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! (1,001 reviews)
"Staff- The staff was mostly kind and helpful. I called the front desk to ask for a refill for the shower gel that was empty, and I was told, “No, we don’t have any.” No explanation, no apology, no alternative options, no . . . hospitality. Amenities-The toiletries (Crabtree & Evelyn) had a nice scent ..."
Reviewed on Jun 23, 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
$130 nightly
The price is $148 total per night from Jul 5 to Jul 6
$148 total
Jul 5 - Jul 6
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)
"Very helpful and responsive staff."
Reviewed on Jun 25, 2026
Hyatt Regency Chesapeake Bay
100 Heron Blvd Cambridge MD
Fully refundableReserve now, pay when you stay
$296 nightly
The price is $336 total per night from Jul 7 to Jul 8
$336 total
Jul 7 - Jul 8
Total with taxes and fees
Book a stay at this beach resort in Cambridge. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
8.8/10 Excellent! (1,003 reviews)
"The grounds were beautiful and well maintained. the staff was very attentive and was able to help whenever i needed it. My wife and i will definitely be back"
Reviewed on Jun 25, 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.
Grace Cottage, St Michaels Walk to everything!
Saint Michaels MD
Stay at this vacation home in St. Michaels. Enjoy laundry facilities, in-room fireplaces, and air conditioning. Popular attractions Saint Marys Square and Saint ...
10/10 Exceptional! (7 reviews)
"This was an AMAZING fine. Grace cottage was so perfectly located where literally everything is walkable and convenient parking for 2 cars. The host, Lisa, was so responsive and just the sweetest. It is clear they want you to have a wonderful time with the cottage being stocked with almost anything ..."
Reviewed on Jun 21, 2026
Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!
Annapolis MD
Stay at this apartment in Annapolis. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Westfield Annapolis Mall and Annapolis Mall Shopping ...
9.6/10 Exceptional! (91 reviews)
"Nathalie was excellent with communication. Property is as described and appears in photos. It is an apartment in a complex. As a few others have noted, there is a smell of cigarette. Sadly, I think it is neighbors smoking in their apartment. Especially in the morning. The apartment is really convenient ..."
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! (249 reviews)
"Great location for USNA. Had everything we needed ready to go for us. Parking and location to the main hub of the town made this house even better. We were able to come and go with the car as needed, but also able to walk easily around town."
Reviewed on Jun 25, 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.
Stay near popular Sherwood attractions
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- U.S. Naval Academy
- Chesapeake Bay
- Sandy Point State Park
- Chesapeake Bay Bridge
- Annapolis City Dock
- Navy-Marine Corps Memorial Stadium
- Breezy Point Beach
- Blackwater National Wildlife Refuge
- Westfield Annapolis Mall
- Anne Arundel Medical Center
- Maryland State House
- Gerry Boyle Park at Great Marsh
- Chesapeake Beach Water Park
- Annapolis Harbor Center Shopping Center
- Queenstown Harbor Golf
- Queenstown Premium Outlets
- Northern Chesapeake Bay
- Annapolis Mall Shopping Center
- Maryland Quiet Waters Park
- Avalon Theatre
- Chesapeake Bay Maritime Museum
- Rod n Reel Charter Fishing
- Chesapeake Bay Environmental Center
- St. Michaels Winery
- Thanksgiving Farm Wines
- Annapolis Landing Marina
