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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 112 Properties in Woodstock
Best Western Woodstock Inn

Best Western Woodstock Inn

990 Lake Avenue, Woodstock
    2.5 out of 5.0
     
     

    Conveniently located near the ski slopes, this Woodstock hotel is within 1 mi (2 km) of McHenry County Fairgrounds, Woodstock City Hall, and Woodstock Square. ...

    Best Western Woodstock Inn$74

    Best Western Woodstock Inn$74
    Quality Inn

    Quality Inn

    1785 South Eastwood Drive, Woodstock
      2.5 out of 5.0
       
       

      Located in the heart of Woodstock, this hotel is within 2 mi (3 km) of McHenry County Fairgrounds, Woodstock City Hall, and Woodstock Square. Woodstock Opera ...

      Quality Inn$55

      Quality Inn$55
      Super 8 by Wyndham Woodstock

      Super 8 by Wyndham Woodstock

      1220 Davis Rd, Woodstock
        2.0 out of 5.0
         
         

        Situated in Woodstock, this motel is within 3 mi (5 km) of McHenry County Fairgrounds, Woodstock City Hall, and Woodstock Square. Woodstock Opera House and Old ...

        Super 8 by Wyndham Woodstock$59

        Super 8 by Wyndham Woodstock$59
        Grand Geneva Resort & Spa

        Grand Geneva Resort & Spa

        7036 Grand Geneva Wy, Lake Geneva
          4.0 out of 5.0
           
           

          Located near the slopes, this Lake Geneva resort is within a 10-minute walk of The Brute Golf Course and The Highlands Golf Course and close to winter sports ...

          Grand Geneva Resort & Spa$169

          Grand Geneva Resort & Spa$169
          Timber Ridge Lodge and Waterpark

          Timber Ridge Lodge and Waterpark

          7020 Grand Geneva Way, Lake Geneva
            3.5 out of 5.0
             
             

            Conveniently located near the ski slopes, this Lake Geneva condo resort is within 1 mi (2 km) of The Brute Golf Course, Dan Patch Stables, and The Highlands ...

            Timber Ridge Lodge and Waterpark$189

            Timber Ridge Lodge and Waterpark$189
            Harbor Shores on Lake Geneva

            Harbor Shores on Lake Geneva

            300 Wrigley Dr, Lake Geneva
              2.5 out of 5.0
               
               

              Located in the heart of Lake Geneva, this hotel is within a 5-minute walk of Riviera Ballroom, Lake Geneva Cruise Line, and Riviera Beach. Geneva Lake Museum ...

              Harbor Shores on Lake Geneva$144

              Harbor Shores on Lake Geneva$144
              Lake Lawn Resort

              Lake Lawn Resort

              2400 E Geneva St, Delavan
                3.5 out of 5.0
                 
                 

                Lake Lawn Resort is 7 minutes by car from the charming antique shops of downtown Delavan. Guests can join a boat tour of Lake Delavan right outside the resort, ...

                Lake Lawn Resort$149

                Lake Lawn Resort$149
                Abbey Resort and Avani Spa

                Abbey Resort and Avani Spa

                269 Fontana Boulevard, Fontana
                  3.5 out of 5.0
                   
                   

                  Offering direct access to the beach, this Fontana resort is 2.8 mi (4.5 km) from Yerkes Observatory and within 6 mi (10 km) of Williams Bay Beach and Black Point ...

                  Abbey Resort and Avani Spa$159

                  Abbey Resort and Avani Spa$159
                  Comfort Suites Elgin

                  Comfort Suites Elgin

                  2480 Bushwood Drive, Elgin
                    2.5 out of 5.0
                     
                     

                    This Elgin, IL hotel is located in the Grove Business Park, 4 miles from the Schaumburg Convention Center. Grand Victoria Casino, Prime Outlets Huntley and Woodfield ...

                    Comfort Suites Elgin$77

                    Comfort Suites Elgin$77
                    Hawthorn Suites by Wyndham Chicago Hoffman Estates

                    Hawthorn Suites by Wyndham Chicago Hoffman Estates

                    2875 Greenspoint Pkwy, Barrington
                      2.5 out of 5.0
                       
                       

                      Situated in Hoffman Estates, this hotel is 1.6 mi (2.6 km) from Bridges of Poplar Creek Country Club and 2.1 mi (3.3 km) from Arboretum of South Barrington. ...

                      Hawthorn Suites by Wyndham Chicago Hoffman Estates$59

                      Hawthorn Suites by Wyndham Chicago Hoffman Estates$59

                      Top Flight Deals

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