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Winter Park Vacations

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

Hotwire can help you find your travel bliss with Winter Park 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 Winter Park

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 Winter Park 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 Winter Park well.

Winter Park Flight + Hotel packages

Top Hotel Deals

See all 173 Hotels in Winter Park
Best Western Alpenglo Lodge

Best Western Alpenglo Lodge

78665 US Hwy 40, Winter Park
    2.5 out of 5.0
     
     

    Located near the slopes, this Winter Park hotel is in the mountains and within 1 mi (2 km) of Winter Park Visitor Center, Grand Park Community Recreation Center, ...

    Best Western Alpenglo Lodge$85

    Best Western Alpenglo Lodge$85
    Trailhead Inn

    Trailhead Inn

    78572 US Hwy 40, Winter Park
      2.5 out of 5.0
       
       

      Situated in the mountains, this motel is within a 15-minute walk of Winter Park Visitor Center, Grand Park Community Recreation Center, and Cozens Ranch House ...

      Trailhead Inn$139

      Trailhead Inn$139
      Vasquez Creek Inn

      Vasquez Creek Inn

      78786 US Hwy 40, Winter Park
        3.5 out of 5.0
         
         

        Conveniently near skiing facilities, this Winter Park hotel is located in the mountains, within 3 mi (5 km) of Winter Park Visitor Center and Winter Park Ski ...

        Vasquez Creek Inn$109

        Vasquez Creek Inn$109
        Timber Run Vista 2 - Studio Room Condo

        Timber Run Vista 2 - Studio Room Condo

        145 Forest Trail, Winter Park
          3.0 out of 5.0
           
           

          Situated in Winter Park, this condo building is close to Winter Park Visitor Center, Grand Park Community Recreation Center, and Cozens Ranch House Museum. Local ...

          Valley Hi Motel

          Valley Hi Motel

          79025 US Hwy 40, Winter Park
            2.0 out of 5.0
             
             

            Situated in Winter Park, this motel is 0.2 mi (0.3 km) from Winter Park Visitor Center and 2.9 mi (4.6 km) from Winter Park Ski Resort. Grand Park Community ...

            Valley Hi Motel$81

            Valley Hi Motel$81
            Silverado II Resort & Event Center

            Silverado II Resort & Event Center

            490 King Crossing Rd., Winter Park
              3.5 out of 5.0
               
               

              Situated in Winter Park, this ski condo building is within 1 mi (2 km) of Winter Park Visitor Center and Grand Park Community Recreation Center. Cozens Ranch ...

              Beaver Village Condos by Staywinterpark

              Beaver Village Condos by Staywinterpark

              50 Village Dr, Winter Park
                3.5 out of 5.0
                 
                 

                Conveniently near skiing facilities, this Winter Park condo building is located in the mountains, within 3 mi (5 km) of Winter Park Visitor Center and Winter ...

                Beaver Village Condos by Staywinterpark$137

                Beaver Village Condos by Staywinterpark$137
                Americas Best Value Inn Sundowner Motel

                Americas Best Value Inn Sundowner Motel

                78869 US Hwy 40, Winter Park
                  2.0 out of 5.0
                   
                   

                  Situated in Winter Park, this motel is 0 mi (0 km) from Winter Park Visitor Center and 3 mi (4.9 km) from Winter Park Ski Resort. Grand Park Community Recreation ...

                  Americas Best Value Inn Sundowner Motel$88

                  Americas Best Value Inn Sundowner Motel$88
                  The Viking Lodge and Ski Shop

                  The Viking Lodge and Ski Shop

                  78966 Main Street, Winter Park
                    2.0 out of 5.0
                     
                     

                    Conveniently near skiing facilities, this Winter Park hotel is located in the mountains, within 3 mi (5 km) of Winter Park Visitor Center and Winter Park Ski ...

                    The Viking Lodge and Ski Shop$55

                    The Viking Lodge and Ski Shop$55
                    Hi Country Haus

                    Hi Country Haus

                    78415 U S Hwy 40, Winter Park
                      2.5 out of 5.0
                       
                       

                      Located near the slopes, this Winter Park condo building is in the mountains and within 1 mi (2 km) of Winter Park Visitor Center, Grand Park Community Recreation ...

                      Top Flight Deals

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