Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Shady Side Vacations

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

Hotwire can help you find your travel bliss with Shady Side 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 Shady Side

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 Shady Side 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 Shady Side well.

Top Hotel Deals

See all 113 Hotels in Shady Side
Country Inn & Suites by Radisson, Washington, D.C. East - Capitol Heights, MD

Country Inn & Suites by Radisson, Washington, D.C. East - Capitol Heights, MD

8850 Hampton Mall Drive North, Capitol Heights
    2.5 out of 5.0
     
     

    Situated in Capitol Heights, this hotel is in the same area as FedEx Field, Six Flags America, and Fort Dupont Park. Regional attractions also include Frederick ...

    Country Inn & Suites by Radisson, Washington, D.C. East - Capitol Heights, MD$87

    Country Inn & Suites by Radisson, Washington, D.C. East - Capitol Heights, MD$87
    La Quinta Inn & Suites DC Metro Capitol Beltway

    La Quinta Inn & Suites DC Metro Capitol Beltway

    55 Hampton Park Blvd, Capitol Heights
      2.5 out of 5.0
       
       

      La Quinta Inn & Suites DC Metro Capitol Beltway offers a comfortable stay with perks, 10 miles (6 km) east of downtown Washington, DC. From the Morgan Boulevard ...

      La Quinta Inn & Suites DC Metro Capitol Beltway$84

      La Quinta Inn & Suites DC Metro Capitol Beltway$84
      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 within 2 mi (3 km) of St. Michaels Winery, St. Michaels Museum, and Chesapeake Bay Maritime Museum. Avalon ...

        St Michaels Inn$86

        St Michaels Inn$86
        Loews Annapolis Hotel

        Loews Annapolis Hotel

        126 West St, Annapolis
           
           

          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 close to Westfield Annapolis Mall, Anne Arundel Medical Center, and Maryland Hall for Creative Arts. Local attractions also ...

            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 close to Westfield Annapolis Mall, Maryland State House, and Anne Arundel Medical Center. Local attractions also include ...

              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$83

                DoubleTree by Hilton Hotel Annapolis$83
                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
                  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 1.1 mi (1.7 km) from Kent Island and within 12 mi (20 km) of Queenstown Premium Outlets and Chesapeake Bay Bridge. Sandy ...

                    Best Western Kent Narrows Inn$97

                    Best Western Kent Narrows Inn$97
                    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

                      Top Flight Deals

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