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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 245 Hotels in Woodstock
Morning Glory B&B Woodstock NY

Morning Glory B&B Woodstock NY

141 Tinker Street, Woodstock
    3.0 out of 5.0
     
     

    Situated in a state park, this bed & breakfast is 0.3 mi (0.5 km) from Woodstock Public Library and 3.1 mi (5 km) from Overlook Mountain Trailhead. Karma Triyana ...

    Hotel Dylan

    Hotel Dylan

    320 Maverick Road, Woodstock
      3.0 out of 5.0
       
       

      Situated in Glenford, this hotel is within 6 mi (10 km) of Woodstock Public Library, Overlook Mountain Trailhead, and Karma Triyana Dharmachakra Monastery. Opus ...

      The Lodge Woodstock

      The Lodge Woodstock

      20 Country Club Lane, Woodstock
        3.5 out of 5.0
         
         

        Situated in Woodstock, this hotel is close to Woodstock Public Library, Overlook Mountain Trailhead, and Karma Triyana Dharmachakra Monastery. Area attractions ...

        Villa Vosilla Boutique Resort

        Villa Vosilla Boutique Resort

        6302 Main St., Tannersville
          3.0 out of 5.0
           
           

          Situated in Tannersville, this resort is 2.6 mi (4.2 km) from Mountain Top Arboretum and within 6 mi (10 km) of Hunter Mountain and Kaaterskill Falls. Windham ...

          Americas Best Value Inn-New Paltz

          Americas Best Value Inn-New Paltz

          7 Terwilliger Ln, New Paltz
            2.0 out of 5.0
             
             

            Situated in New Paltz, this motel is within 2 mi (3 km) of State University of New York-New Paltz, G. Steve Jordan Gallery, and Loren Campbell Memorial Field. ...

            Americas Best Value Inn-New Paltz$77

            Americas Best Value Inn-New Paltz$77
            The Wick, Hudson, A Tribute Portfolio Hotel

            The Wick, Hudson, A Tribute Portfolio Hotel

            41 Cross Street, Hudson
              4.0 out of 5.0
               
               

              Situated in Hudson, this boutique hotel is close to Max and Lillian Katzman Theater, Hudson Opera House, and Hudson Area Library. Local attractions also include ...

              The Wick, Hudson, A Tribute Portfolio Hotel$152

              The Wick, Hudson, A Tribute Portfolio Hotel$152
              Residence Inn by Marriott Kingston

              Residence Inn by Marriott Kingston

              800 Frank Sottile Boulevard, Kingston
                3.0 out of 5.0
                 
                 

                Situated in Kingston, this hotel is 0.3 mi (0.5 km) from Hudson Valley Mall and within 6 mi (10 km) of Ulster Performing Arts Center and Old Dutch Church. Senate ...

                Residence Inn by Marriott Kingston$110

                Residence Inn by Marriott Kingston$110
                Comfort Inn Saugerties

                Comfort Inn Saugerties

                2790 Route 32, Saugerties
                  2.5 out of 5.0
                   
                   

                  Situated in Saugerties, this hotel is within 3 mi (5 km) of Saugerties Village Beach, Seamon Park, and Kiwanis Ice Arena. HITS-on-the-Hudson is 2.6 mi (4.2 km) ...

                  Comfort Inn Saugerties$100

                  Comfort Inn Saugerties$100
                  Super 8 Kingston

                  Super 8 Kingston

                  487 Washington Ave, Kingston
                    2.0 out of 5.0
                     
                     

                    Situated in Kingston, this motel is within a 15-minute walk of Senate House State Historic Site, Forsyth Park, and Volunteer Fireman's Hall and Museum of Kingston. ...

                    Super 8 Kingston$64

                    Super 8 Kingston$64
                    SunView Motel

                    SunView Motel

                    5844 Main St, Tannersville
                      2.5 out of 5.0
                       
                       

                      Situated in Tannersville, this motel is 2.5 mi (4.1 km) from Mountain Top Arboretum and within 6 mi (10 km) of Kaaterskill Falls and Hunter Mountain. Bailiwick ...

                      SunView Motel$99

                      SunView Motel$99

                      Top Flight Deals

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