Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5
Due to coronavirus (COVID-19) travel advisories, some destinations may be unavailable for certain dates. Find out more.

Explore thousands of activities with free cancellation and no added fees.

Design your experience with airport transfers, excursions, day tours & more.

Get an insider's look in what to book before you travel.


Top 10 Things To Do In Woodstock

See all 15 things to do in Springfield

Most Popular Booked Woodstock Hotels

Woodstock Inn & Resort $268
Woodstock Inn & Resort

Woodstock Inn & Resort

Fourteen The Green, Woodstock, VT
     
    5.0
    of 5, from 3 reviews
    4.5 out of 5.0 Stars

    This smoke-free resort features a golf course, a full-service spa, and 4 restaurants. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at one of the 2 bars/lounges and enjoy the 2 indoor tennis courts and indoor pool.

    The Blue Horse Inn $218
    The Blue Horse Inn

    The Blue Horse Inn

    3 Church Street, Woodstock, VT
       
      5.0
      of 5, from 1 reviews
      3.5 out of 5.0 Stars

      A seasonal outdoor pool is featured at this bed & breakfast, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a library are also on offer.

      The Jackson House Inn $224
      The Jackson House Inn

      The Jackson House Inn

      43 Senior Lane, Woodstock, VT
         
        5.0
        of 5, from 2 reviews
        4.0 out of 5.0 Stars

        A bar/lounge and a terrace are featured at this bed & breakfast, along with free self parking. Guests will appreciate free perks like full breakfast and WiFi in public areas. A garden, a lobby fireplace, and a picnic area are also on offer.

        The Woodstocker B&B $186
        The Woodstocker B&B

        The Woodstocker B&B

        61 River St, Woodstock, VT
           
          5.0
          of 5, from 1 reviews
          4.0 out of 5.0 Stars

          A sauna, free self parking, and free newspapers are featured at this bed & breakfast. Guests will appreciate free perks like cooked-to-order breakfast and WiFi in public areas. A terrace, a garden, and a snack bar/deli are also on offer.

          Braeside Lodging $128
          Braeside Lodging

          Braeside Lodging

          908 East Woodstock Road, Woodstock, VT
             
            5.0
            of 5, from 1 reviews
            2.0 out of 5.0 Stars

            This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace and a garden are also provided.

            506 On the River Inn $159
            506 On the River Inn

            506 On the River Inn

            1653 West Woodstock Road, Woodstock, VT
               
              4.9
              of 5, from 12 reviews
              4.0 out of 5.0 Stars

              This hotel features an indoor pool, a spa tub, and a restaurant. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the fitness center and perks like free self parking and a free ski shuttle.

              The Shire Woodstock $129
              The Shire Woodstock

              The Shire Woodstock

              46 Pleasant St., Woodstock, VT
                 
                4.7
                of 5, from 7 reviews
                3.0 out of 5.0 Stars

                This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and a picnic area are also provided.

                The Village Inn of Woodstock Get Rates
                The Village Inn of Woodstock

                The Village Inn of Woodstock

                41 Pleasant Street, Woodstock, VT
                   
                  4.0 out of 5.0 Stars

                  A bar/lounge and a terrace are featured at this inn, along with free self parking. Guests will appreciate free perks like full breakfast and WiFi in public areas. A garden and concierge services are also provided.

                  Places To Go In Woodstock

                  Welcome, traveler, to Woodstock. Your journey has landed you here, and new adventures are calling your name. Now that you’ve arrived, you can stay in the safety and comfort of your hotel and watch the world spin past…or you can embrace this new place you’ve come to. Learn its streets. Meet its people. Learn its history. Your hand is already on the doorknob, isn’t it?

                  Things to Do in Woodstock

                  You’ll not be wanting for things to do in Woodstock. Explore the downtown area in search of museums and boutiques…or that next delicious meal. What tickles your fancy? A delectable five-course supper at the restaurant you’ve been hearing about? Or perhaps you’d rather read the paper while sipping hot coffee at one of the cafes scattered throughout town. Take in a show at the theatre, or just walk along down the main thoroughfare, watching people wander past.

                  Why spend hours ruminating over what to do in Woodstock? Let the possibilities wash over you as you explore this new region. Move out on foot and get to know the area on a more personal level. Find that perfect souvenir at one of the smaller shops, or reinvent your entire artistic aesthetic at your new favorite gallery.

                  Is the wind whispering suggestions in your mind? Rent a car and take it out beyond city limits and into the wild blue yonder. Explore the smaller cities and towns past the border, and get to know the stories behind them. Visit a county fair and let childhood memories wash over you as cotton candy melts in your mouth. Sample hand-made jam at a stop on a forgotten highway, or let the hustle and bustle of modern life sweep you away as you lose yourself in the organized chaos of a modern metropolis. Your choices are endless—and so are the adventures to come.

                  When you book your journey with Travelocity, you’re never far from Woodstock attractions. After all, the money you save when you plan a trip with us is best spent along the way. Whether it’s the roar of the city you crave, or the quiet solitude that comes with a simpler getaway, everything you need to get started is right here.