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! (1,005 reviews)
"It would have been nice to have a heated indoor pool and jacuzzi. The food was excellent. The staff was excellent. I found the room to be too small."
Reviewed on Jun 26, 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $144 total per night from Jul 7 to Jul 8
$144 total
Jul 7 - Jul 8
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! (1,866 reviews)
"To be honest, it was a little confusing. We arrived close to midnight, and our room was located in a different building than the registration desk. We're very good at getting lost, and fortunately the bartender from the hotel saw us wandering around the state house with our suitcases, and pointed ..."
Reviewed on Jun 27, 2026
Hyatt Regency Chesapeake Bay
100 Heron Blvd Cambridge MD
$296 nightly
The price is $336 total per night from Jul 6 to Jul 7
$336 total
Jul 6 - Jul 7
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! (1,000 reviews)
"Dealing with billing issue. Other than that, great place to stay."
Reviewed on Jun 26, 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.
ST. MICHAELS ESTATE OFFERS WATERFRONT POOL, PIER, DOCK AND 15 ACS
PET FRIENDLY
Sherwood MD
Book a stay at this family-friendly vacation home in Sherwood. Enjoy free WiFi, private pools, and breakfast (surcharge). Popular attractions Goat Island and ...
10/10 Exceptional! (41 reviews)
"This property is a dream for a family--large house with plenty of room, beautiful location on Dunn Cove and a great pool. The house really has two parts which are complete in themselves with each having a kitchen and laundry. This allowed for my family members to have both privacy and together time. ..."
Reviewed on Jun 16, 2026
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
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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- Visit Oxon Hill
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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
