Name: Historic Inns of Annapolis
Price range: CA $180
Rating: 9

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Your Sherwood Vacation

When you organize a vacation package to Sherwood, you can relax and enjoy your getaway knowing that all your travel arrangements have been made in advance. Discover the charms of this vibrant city while based in a neighborhood like Deale Beach, which is good for walking. A trip to Sherwood is an excellent opportunity to take in the sights. Check out renowned attractions like St. Michaels Winery, Chesapeake Bay Maritime Museum and Tilghman Watermen’s Museum. Whoever you're escaping with and whatever your bank balance, your dream Sherwood vacation is only clicks away with Expedia.

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Sherwood Hotel Deals

Knapps Narrows Marina & Inn

6176 Tilghman Island Road Sherwood MD

Fully refundableReserve now, pay when you stay

CA $209

CA $230 total

Apr 13 - Apr 14

includes taxes & fees

9.4/10 Exceptional! (377 reviews)

Parking was easy, could see car from room, coffee and tea offered all day, bike sign out was easy

Reviewed on Apr 2, 2026

Graduate by Hilton Annapolis

126 West St Annapolis MD

Fully refundableReserve now, pay when you stay

CA $255

CA $291 total

Apr 19 - Apr 20

includes taxes & fees

9.4/10 Exceptional! (1,003 reviews)

It was the perfect location for our activities

Reviewed on Apr 5, 2026

Historic Inns of Annapolis

58 State Circle Annapolis MD

Fully refundableReserve now, pay when you stay

CA $180

CA $253 total

Apr 19 - Apr 20

includes taxes & fees

9/10 Wonderful! (1,868 reviews)

Great historic building… felt like home away from home.

Reviewed on Apr 4, 2026

See all 1,158 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.