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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.

Woodstock Flight + Hotel packages

Top Hotel Deals

See all 96 Hotels in Woodstock
Comfort Inn Woodstock Shenandoah

Comfort Inn Woodstock Shenandoah

1011 Motel Dr, Woodstock
    2.5 out of 5.0
     
     

    Located in the heart of Woodstock, this hotel is within 1 mi (2 km) of Shenandoah County Fairgrounds and W.O. Riley Park. Woodstock Museum and 7 East Gallery ...

    Comfort Inn Woodstock Shenandoah$92

    Comfort Inn Woodstock Shenandoah$92
    Hampton Inn & Suites Woodstock

    Hampton Inn & Suites Woodstock

    1150 Motel Dr, Woodstock
      2.5 out of 5.0
       
       

      Situated in Woodstock, this hotel is within 1 mi (2 km) of Shenandoah County Fairgrounds and W.O. Riley Park. Woodstock Museum and 7 East Gallery are also within ...

      Hampton Inn & Suites Woodstock$97

      Hampton Inn & Suites Woodstock$97
      Holiday Inn Express Woodstock-Shenandoah Valley

      Holiday Inn Express Woodstock-Shenandoah Valley

      1130 Motel Dr, Woodstock
        2.5 out of 5.0
         
         

        Situated in Woodstock, this hotel is within 1 mi (2 km) of Shenandoah County Fairgrounds and W.O. Riley Park. Woodstock Museum and 7 East Gallery are also within ...

        Holiday Inn Express Woodstock-Shenandoah Valley$100

        Holiday Inn Express Woodstock-Shenandoah Valley$100
        Econo Lodge

        Econo Lodge

        1290 S Main St, Woodstock
          2.0 out of 5.0
           
           

          Situated in the mountains, this hotel is 1.1 mi (1.7 km) from Shenandoah County Fairgrounds and within 3 mi (5 km) of 7 East Gallery and W.O. Riley Park. Woodstock ...

          Econo Lodge$65

          Econo Lodge$65
          Days Inn by Wyndham Luray Shenandoah

          Days Inn by Wyndham Luray Shenandoah

          138 Whispering Hill Rd, Luray
            2.0 out of 5.0
             
             

            Located in Thorton Gap Entrance Shenandoah, 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 ...

            Days Inn by Wyndham Luray Shenandoah$67

            Days Inn by Wyndham Luray Shenandoah$67
            Days Inn by Wyndham New Market Battlefield

            Days Inn by Wyndham New Market Battlefield

            9360 George Collin Pkwy, New Market
              2.0 out of 5.0
               
               

              Located in Thorton Gap Entrance Shenandoah, this motel is within a 10-minute walk of New Market Battlefield and Hall of Valor Civil War Museum. Endless Caverns ...

              Days Inn by Wyndham New Market Battlefield$59

              Days Inn by Wyndham New Market Battlefield$59
              Mimslyn Inn Historic Hotels Of America

              Mimslyn Inn Historic Hotels Of America

              401 W Main St, Luray
                3.0 out of 5.0
                 
                 

                Located in Thorton Gap Entrance Shenandoah, this historic hotel is within 1 mi (2 km) of Warehouse Art Gallery and Luray Caverns. Car and Carriage Caravan Museum ...

                Mimslyn Inn Historic Hotels Of America$125

                Mimslyn Inn Historic Hotels Of America$125
                Motel 6 MT. Jackson - Shenandoah

                Motel 6 MT. Jackson - Shenandoah

                250 Conicville Blvd, Mount Jackson
                  2.0 out of 5.0
                   
                   

                  Located in Thorton Gap Entrance Shenandoah, this motel is within 6 mi (10 km) of Meems Bottom Covered Bridge, Kindred Pointe Winery, and Yellow Barn at Shenandoah ...

                  Motel 6 MT. Jackson - Shenandoah$65

                  Motel 6 MT. Jackson - Shenandoah$65
                  Super 8 by Wyndham Front Royal

                  Super 8 by Wyndham Front Royal

                  111 South St, Front Royal
                    2.0 out of 5.0
                     
                     

                    Located in Front Royal Entrance Shenandoah National Park, this hotel is within a 10-minute walk of Blue Ridge Arts Council and Gallery and Front Royal Visitor's ...

                    Super 8 by Wyndham Front Royal$54

                    Super 8 by Wyndham Front Royal$54
                    Hotel Laurance

                    Hotel Laurance

                    2 South Court Street, Luray
                      3.5 out of 5.0
                       
                       

                      Located in Thorton Gap Entrance Shenandoah, this boutique hotel is within 1 mi (2 km) of Warehouse Art Gallery, Luray Caverns, and Car and Carriage Caravan Museum. ...

                      Top Flight Deals

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