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Woodstock Vacations

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

Hotwire can help you find your travel bliss with Woodstock 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 Woodstock

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 Woodstock 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 Woodstock well.

Top Hotel Deals

See all 578 Hotels in Woodstock
The Shire Woodstock

The Shire Woodstock

46 Pleasant St., Woodstock
    3.0 out of 5.0
     
     

    Situated in Woodstock, this hotel is within a 15-minute walk of Dana House Museum, Billings Park and Trail, and Woodstock Town Hall Theatre. Mount Tom Peak and ...

    506 On the River Inn

    506 On the River Inn

    1653 West Woodstock Road, Woodstock
      4.0 out of 5.0
       
       

      This family-friendly West Woodstock hotel is located in the historical district, within 2 mi (3 km) of Union Arena Community Center, Marsh-Billings-Rockefeller ...

      Woodstock Inn & Resort

      Woodstock Inn & Resort

      Fourteen The Green, Woodstock
        3.5 out of 5.0
         
         

        Situated in Woodstock, this resort is within a 5-minute walk of Woodstock Town Hall Theatre and Dana House Museum. Billings Park and Trail and Mount Tom Peak ...

        Woodstock Inn & Resort$185

        Woodstock Inn & Resort$185
        The Charleston House Bed & Breakfast

        The Charleston House Bed & Breakfast

        21 Pleasant Street, Woodstock
          3.0 out of 5.0
           
           

          Situated in Woodstock, this bed & breakfast is within a 10-minute walk of Dana House Museum and Billings Park and Trail. Woodstock Town Hall Theatre and Mount ...

          Sleep Woodstock Motel

          Sleep Woodstock Motel

          4324 West Woodstock Road, Woodstock
            2.0 out of 5.0
             
             

            Situated on a river, this motel is within 6 mi (10 km) of Union Arena Community Center, Long Trail Brewing Company, and Marsh-Billings-Rockefeller National Historical ...

            Braeside Lodging

            Braeside Lodging

            908 East Woodstock Road, Woodstock
              2.0 out of 5.0
               
               

              Situated in Woodstock, this motel is within 2 mi (3 km) of Dana House Museum, Billings Park and Trail, and Woodstock Town Hall Theatre. Mount Tom Peak and Billings ...

              The Village Inn of Woodstock

              The Village Inn of Woodstock

              41 Pleasant Street, Woodstock
                4.0 out of 5.0
                 
                 

                Situated in Woodstock, this inn is close to Billings Park and Trail, Dana House Museum, and Billings Farm and Museum. Also nearby are Woodstock Town Hall Theatre ...

                The Jackson House Inn

                The Jackson House Inn

                43 Senior Lane, Woodstock
                  4.0 out of 5.0
                   
                   

                  Situated in West Woodstock, this bed & breakfast is within 2 mi (3 km) of Union Arena Community Center, Marsh-Billings-Rockefeller National Historical Park, ...

                  The Lincoln Inn & Restaurant At The Covered Bridge

                  The Lincoln Inn & Restaurant At The Covered Bridge

                  2709 W. Woodstock Road, Woodstock
                    3.5 out of 5.0
                     
                     

                    Situated in West Woodstock, this inn is within 3 mi (5 km) of Union Arena Community Center, Marsh-Billings-Rockefeller National Historical Park, and Woodstock ...

                    Deer Brook Inn

                    Deer Brook Inn

                    4548 West Woodstock Road, Woodstock
                      4.0 out of 5.0
                       
                       

                      Situated in the mountains, this bed & breakfast is within 6 mi (10 km) of Union Arena Community Center, Long Trail Brewing Company, and Marsh-Billings-Rockefeller ...

                      Top Flight Deals

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