Sherwood, MD

Travel Guide

Gardens and large home at Sherwood Gardens Park, in Baltimore, M
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
$146 nightly
The price is $166 total per night from Jul 1 to Jul 2
$166 total
Jul 1 - Jul 2
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! (1,871 reviews)
"Excellent location, walking distance to everything we had plans on seeing"

Reviewed on Jun 9, 2026

Historic Inns of Annapolis
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd Cambridge MD
$352 nightly
The price is $400 total per night from Jul 6 to Jul 7
$400 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! (1,007 reviews)
"The hotel was very nice enjoyed my stay."

Reviewed on Jun 8, 2026

Hyatt Regency Chesapeake Bay
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
$111 nightly
The price is $127 total per night from Jun 15 to Jun 16
$127 total
Jun 15 - Jun 16
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 ...
8.8/10 Excellent! (1,015 reviews)
"The bed and sheets were very comfortable for quality sleeping. Nice towels as well. Air conditioning was loud. The attached restaurant had wonderful food. The pool was great, even a lifeguard on duty! The traffic unfortunately is loud from the highway."

Reviewed on Jun 9, 2026

DoubleTree by Hilton Hotel Annapolis
See all 1,160 properties in Sherwood
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.
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

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! (248 reviews)
"The house is in a great location. It is very historic and the inside is quaint as you would expect in a historic house. The single garage is around the corner and a tight squeeze. You have to either double park in front to unload (not ideal on a busy street corner) or unload at the garage and walk ..."

Reviewed on Jun 9, 2026

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Chesapeake Houseboat Getaway on Kent Island, Maryland

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! (58 reviews)
"I have stayed at many places over the years. This would be my favorite place. The view and the location was unbelievable. We were in town for a wedding and our host let us check in early to accommodate the wedding schedule. I would definitely recommend this house boat to anyone that wants a unique ..."

Reviewed on Jun 1, 2026

Chesapeake Houseboat Getaway on Kent Island, Maryland
Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock

Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock

Bozman MD
Stay at this cottage in Bozman. Enjoy air conditioning. Popular attractions Neavitt Park and Back Creek Park are located nearby.
Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock
See all properties in Sherwood
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.

Back Creek Community Park

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.

Goat Island

Cities near Sherwood

Sunrise kayaking

Tilghman

Oxford to Bellevue Ferry, Maryland, continuous use from 1683 to 1836

Bozman

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