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Annapolis Vacations

Pack those stellar shades. We have Annapolis 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 Annapolis – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Annapolis 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 Annapolis

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 Annapolis 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 Annapolis well.

Top Hotel Deals

See all 1,224 Properties in Annapolis
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
    Country Inn & Suites by Radisson, Annapolis, MD

    Country Inn & Suites by Radisson, Annapolis, MD

    2600 Housley Road, Annapolis
      3.0 out of 5.0
       
       

      Situated in a shopping district, this hotel is 0.8 mi (1.2 km) from Westfield Annapolis Mall and 1.4 mi (2.2 km) from Anne Arundel Medical Center. Maryland State ...

      Country Inn & Suites by Radisson, Annapolis, MD$93

      Country Inn & Suites by Radisson, Annapolis, MD$93
      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 (2.7 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
        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 km) from Anne Arundel Medical Center. Maryland State House and ...

          Hilton Garden Inn Annapolis$101

          Hilton Garden Inn Annapolis$101
          Comfort Inn Conference Center

          Comfort Inn Conference Center

          4500 Crain Hwy, Bowie
            3.0 out of 5.0
             
             

            Situated in the business district, this hotel is 0.9 mi (1.4 km) from Prince George's Stadium and within 3 mi (5 km) of Allen Pond Park and National Capital ...

            Comfort Inn Conference Center$99

            Comfort Inn Conference Center$99
            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$83

              DoubleTree by Hilton Hotel Annapolis$83
              Historic Inns of Annapolis

              Historic Inns of Annapolis

              58 State Circle, Annapolis
                3.5 out of 5.0
                 
                 

                These central Annapolis inns, located within a half-mile (.8 kilometers) of the US Naval Academy, comprise 3 buildings: the 1727 Governor Calvert House, the ...

                Historic Inns of Annapolis$169

                Historic Inns of Annapolis$169
                Comfort Inn Annapolis

                Comfort Inn Annapolis

                76 Old Mill Bottom Rd. N, Annapolis
                  2.5 out of 5.0
                   
                   

                  Situated in Annapolis, this hotel is within 6 mi (10 km) of U.S. Naval Academy Golf Club, U.S. Naval Academy, and William Paca House. Maryland State House and ...

                  Comfort Inn Annapolis$104

                  Comfort Inn Annapolis$104
                  Best Western Annapolis

                  Best Western Annapolis

                  2520 Riva Rd, Annapolis
                    2.5 out of 5.0
                     
                     

                    Situated in the business district, this hotel is 0.9 mi (1.4 km) from Westfield Annapolis Mall and within 3 mi (5 km) of Anne Arundel Medical Center and Maryland ...

                    Best Western Annapolis$81

                    Best Western Annapolis$81
                    SpringHill Suites by Marriott Annapolis

                    SpringHill Suites by Marriott Annapolis

                    189 Admiral Cochrane Drive, Annapolis
                      3.0 out of 5.0
                       
                       

                      Situated in Annapolis, this hotel is 1.7 mi (2.7 km) from Westfield Annapolis Mall and 2.1 mi (3.3 km) from Anne Arundel Medical Center. Maryland State House ...

                      SpringHill Suites by Marriott Annapolis$89

                      SpringHill Suites by Marriott Annapolis$89

                      Top Flight Deals

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