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Sherwood Vacations

Pack those stellar shades. We have Sherwood vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Sherwood – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Sherwood vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Sherwood

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Sherwood vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Sherwood well.

Top Hotel Deals

See all 116 Hotels in Sherwood
Lowes Wharf Marina Inn

Lowes Wharf Marina Inn

21651 Lowes Wharf Rd, Sherwood
    3.0 out of 5.0
     
     

    Situated on the waterfront, this inn is 4.4 mi (7.1 km) from Tilghman Watermen’s Museum and 9.9 mi (16 km) from St. Michaels Museum. Avalon Theatre and Academy ...

    St Michaels Inn

    St Michaels Inn

    1228 S Talbot Street, St. Michaels
      2.5 out of 5.0
       
       

      Situated in the historical district, this hotel is 1.3 mi (2.2 km) from St. Michaels Museum and within 9 mi (15 km) of Historical Society of Talbot County and ...

      St Michaels Inn$86

      St Michaels Inn$86
      Loews Annapolis Hotel

      Loews Annapolis Hotel

      126 West St, Annapolis
        4.0 out of 5.0
         
         

        This six-story brick hotel is 0.5 mile from the shops, restaurants, and historic sites of Annapolis and 1 mile from both the Naval Academy and City Dock on Chesapeake ...

        Loews Annapolis Hotel$151

        Loews Annapolis Hotel$151
        Hilton Garden Inn Annapolis

        Hilton Garden Inn Annapolis

        305 Harry S Truman Pkwy, Annapolis
          3.0 out of 5.0
           
           

          Situated in Annapolis, this hotel is 1.5 mi (2.4 km) from Westfield Annapolis Mall and 1.9 mi (3.1 km) from Anne Arundel Medical Center. Maryland State House ...

          Hilton Garden Inn Annapolis$101

          Hilton Garden Inn Annapolis$101
          Extended Stay America Annapolis - Womack Drive

          Extended Stay America Annapolis - Womack Drive

          1 Womack Dr, Annapolis
            2.5 out of 5.0
             
             

            Situated in Annapolis, this hotel is 1.7 mi (2.8 km) from Westfield Annapolis Mall and 2.1 mi (3.3 km) from Anne Arundel Medical Center. Maryland State House ...

            Extended Stay America Annapolis - Womack Drive$81

            Extended Stay America Annapolis - Womack Drive$81
            DoubleTree by Hilton Hotel Annapolis

            DoubleTree by Hilton Hotel Annapolis

            210 Holiday Court, Annapolis
              3.5 out of 5.0
               
               

              This Doubletree hotel is surrounded by dining and shopping, 28 miles to DC or Baltimore. 18 miles to BWI or the Metro. Free shuttle within 5 miles. 3 miles to ...

              DoubleTree by Hilton Hotel Annapolis$111

              DoubleTree by Hilton Hotel Annapolis$111
              Best Western Kent Narrows Inn

              Best Western Kent Narrows Inn

              3101 Main Street, Grasonville
                2.5 out of 5.0
                 
                 

                Situated in Grasonville, this motel is within 12 mi (20 km) of Queenstown Premium Outlets, Chesapeake Bay Bridge, and Sandy Point State Park. U.S. Naval Academy ...

                Best Western Kent Narrows Inn$94

                Best Western Kent Narrows Inn$94
                Hampton Inn & Suites Annapolis

                Hampton Inn & Suites Annapolis

                124 Womack Dr, Annapolis
                  2.5 out of 5.0
                   
                   

                  Situated in the business district, this hotel is 1.5 mi (2.4 km) from Westfield Annapolis Mall and 1.9 mi (3.1 km) from Anne Arundel Medical Center. Maryland ...

                  Hampton Inn & Suites Annapolis$93

                  Hampton Inn & Suites Annapolis$93
                  Holiday Inn Express & Suites Annapolis

                  Holiday Inn Express & Suites Annapolis

                  2451 Riva Rd, Annapolis
                    2.5 out of 5.0
                     
                     

                    Situated in the historical district, this hotel is 0.5 mi (0.8 km) from Westfield Annapolis Mall and within 3 mi (5 km) of Maryland State House and William Paca ...

                    Holiday Inn Express & Suites Annapolis$99

                    Holiday Inn Express & Suites Annapolis$99
                    Annapolis Waterfront Hotel, Autograph Collection

                    Annapolis Waterfront Hotel, Autograph Collection

                    80 Compromise St, Annapolis
                      3.5 out of 5.0
                       
                       

                      Located in the heart of Annapolis, this hotel is within a 10-minute walk of William Paca House, Maryland State House, and Hammond-Harwood House. U.S. Naval Academy ...

                      Annapolis Waterfront Hotel, Autograph Collection$239

                      Annapolis Waterfront Hotel, Autograph Collection$239

                      Top Flight Deals

                      Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.