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Boston Vacations

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

Hotwire can help you find your travel bliss with Boston 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 Boston

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 Boston 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 Boston well.

Boston Flight + Hotel packages

Top Hotel Deals

See all 50 Properties in Boston
The Inn on Thistle Hill

The Inn on Thistle Hill

5541 Sperryville Pike, Boston
    2.5 out of 5.0
     
     

    Situated in the mountains, this bed & breakfast is within 12 mi (20 km) of Copper Fox Distillery, Gadino Cellars, and St. Stephen's Episcopal Church. The State ...

    The Inn on Thistle Hill$165

    The Inn on Thistle Hill$165
    Days Inn by Wyndham Luray Shenandoah

    Days Inn by Wyndham Luray Shenandoah

    138 Whispering Hill Rd, Luray
      2.0 out of 5.0
       
       

      Situated in Luray, this hotel is 2.3 mi (3.7 km) from Warehouse Art Gallery and within 6 mi (10 km) of Luray Caverns and Car and Carriage Caravan Museum. The ...

      Days Inn by Wyndham Luray Shenandoah$72

      Days Inn by Wyndham Luray Shenandoah$72
      Best Western Culpeper Inn

      Best Western Culpeper Inn

      U.s 29 Business S, Culpeper
        2.5 out of 5.0
         
         

        Situated in Culpeper, this hotel is within 3 mi (5 km) of The State Theatre, The Museum of Culpeper History, and St. Stephen's Episcopal Church. Culpeper National ...

        Best Western Culpeper Inn$90

        Best Western Culpeper Inn$90
        The Inn At Little Washington

        The Inn At Little Washington

        Middle And Main Streets, Washington
          5.0 out of 5.0
           
           

          Situated in a rural location, this luxury hotel is steps from The Theatre at Washington and The First Washington of All Monument. Little Washington Winery is ...

          The Inn At Little Washington$755

          The Inn At Little Washington$755
          Microtel Inn & Suites by Wyndham Culpeper

          Microtel Inn & Suites by Wyndham Culpeper

          885 Willis Ln, Culpeper
            2.0 out of 5.0
             
             

            Situated in Culpeper, this hotel is within 3 mi (5 km) of The State Theatre, The Museum of Culpeper History, and St. Stephen's Episcopal Church. Culpeper National ...

            Microtel Inn & Suites by Wyndham Culpeper$60

            Microtel Inn & Suites by Wyndham Culpeper$60
            Red Carpet Inn

            Red Carpet Inn

            13065 James Madison Hwy, Culpeper
              2.0 out of 5.0
               
               

              Situated in Culpeper, this motel is within 3 mi (5 km) of Library of Congress National Audio Visual Conservation Center, The State Theatre, and The Museum of ...

              Red Carpet Inn$65

              Red Carpet Inn$65
              Quality Inn

              Quality Inn

              890 Willis Ln, Culpeper
                2.5 out of 5.0
                 
                 

                Located in the heart of Culpeper, this hotel is within 3 mi (5 km) of The State Theatre, The Museum of Culpeper History, and St. Stephen's Episcopal Church. ...

                Quality Inn$85

                Quality Inn$85
                Skyland Resort

                Skyland Resort

                Milepost 41 7 42 5 Skyline Drive, Luray
                  2.0 out of 5.0
                   
                   

                  This family-friendly Luray hotel is located in a national park, 0.5 mi (0.8 km) from Stony Man, and within 12 mi (20 km) of Dark Hollow Falls and Rose River ...

                  Skyland Resort$170

                  Skyland Resort$170
                  Red Roof Inn Culpeper

                  Red Roof Inn Culpeper

                  889 Willis Lane, Culpeper
                    2.0 out of 5.0
                     
                     

                    Located in the heart of Culpeper, this hotel is within 3 mi (5 km) of The State Theatre, The Museum of Culpeper History, and St. Stephen's Episcopal Church. ...

                    Red Roof Inn Culpeper$64

                    Red Roof Inn Culpeper$64
                    Cardinal Inn

                    Cardinal Inn

                    1005 East Main Street, Luray
                      2.5 out of 5.0
                       
                       

                      Situated in Luray, this hotel is 1.1 mi (1.7 km) from Warehouse Art Gallery and 2.3 mi (3.7 km) from Luray Caverns. Car and Carriage Caravan Museum and The Garden ...

                      Cardinal Inn$70

                      Cardinal Inn$70

                      Top Flight Deals

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