
Sherwood Holiday Packages
Save when you book Sherwood package deals

Book your Sherwood holiday
Want to save some hard-earned cash with Wotif?
Our accommodation and flight package deals are truly unbeatable.
With the extra finances you'll be able to see even more in Sherwood.
If you act fast, you can save as much as . And think of the choices you have with more than 550 airlines and 665,000 properties, it's so easy to design your ideal holiday.
Wotif boasts some of the best prices under the sun. So quit daydreaming and start making new experiences.
Sherwood Accommodation
With just 5 accommodations in Sherwood, securing somewhere to stay should be number one on your to-do list. Wotif has some awesome deals available today, so what are you waiting for?
Busy dusting off your passport for your upcoming holiday? No time to browse the web for hours for a place to stay? Why not choose from one of our top suggestions? The Tilghman Island Inn and Lazyjack Inn on Dogwood Harbour are among the best properties in this locale.
Holidays to Sherwood
Love going to places you've never been? Us too. But you don't have to get yourself lost along the way. Look over our guide to Sherwood and you'll be swanning around like a proper local in next to no time.Sherwood is within easy driving distance of a couple of noteworthy cities. You can reach this town from Shady Side, which is 19 kilometres away to the northwest. Chesapeake Beach is also just 19 kilometres to the west.
Top Sherwood hotels

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
What a spectacular home!! We all loved our stay and took advantage of the beautiful heated pool, dock, fire pit and playground. In the evening the pool table, ping pong and foosball were enjoyed by all. Stunning views, beautiful furnishings and comfortable bedding. Hopefully we will have occasion ...
Reviewed on 20 Oct 2025

Graduate by Hilton Annapolis
Wonderfully. We were pleasantly surprised at the hotel. Very nice. Well decorated. Convenient and walkable location.
Reviewed on 20 Oct 2025

Historic Inns of Annapolis
All was very good except: no soap at sink in bathroom and none could be “found.” There was a coffee pot that had to be replaced with one that could work with the type coffee pods provided. Promptly replaced, but how could housekeeping have an outdated coffee maker for older-type coffee filter ...
Reviewed on 28 Oct 2025
