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Osceola Vacations

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

Hotwire can help you find your travel bliss with Osceola 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 Osceola

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 Osceola 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 Osceola well.

Top Hotel Deals

See all 53 Hotels in Osceola
River Valley Inn & Suites

River Valley Inn & Suites

1030 N Cascade Street, Osceola
    2.5 out of 5.0
     
     

    Situated in Osceola, this motel is 1 mi (1.6 km) from Riverwood Canoe and 1.4 mi (2.2 km) from Osceola & St. Croix Valley Railway. St. Croix Festival Theatre ...

    Asteria Inn & Suites - Stillwater/St. Paul

    Asteria Inn & Suites - Stillwater/St. Paul

    2190 W Frontage Rd, Stillwater
      2.5 out of 5.0
       
       

      Situated in Stillwater, this hotel is in the same area as Phipps Center for the Arts, Seasons on St. Croix Gallery, and StoneRidge Golf Club. Regional attractions ...

      Asteria Inn & Suites - Stillwater/St. Paul$49

      Asteria Inn & Suites - Stillwater/St. Paul$49
      Water Street Inn

      Water Street Inn

      101 Water St South, Stillwater
        3.5 out of 5.0
         
         

        Situated in Stillwater, this hotel is within 9 mi (15 km) of Phipps Center for the Arts, Seasons on St. Croix Gallery, and Somerset Amphitheater. Float Rite ...

        Comfort Inn & Suites

        Comfort Inn & Suites

        2000 Washington Avenue, Stillwater
          2.5 out of 5.0
           
           

          Situated in Stillwater, this hotel is within 12 mi (20 km) of StoneRidge Golf Club, Seasons on St. Croix Gallery, and Phipps Center for the Arts. Maplewood Mall ...

          Comfort Inn & Suites$89

          Comfort Inn & Suites$89
          Best Western Plus White Bear Country Inn

          Best Western Plus White Bear Country Inn

          4940 Highway 61 North, White Bear Lake
            3.0 out of 5.0
             
             

            This family-friendly White Bear Lake hotel is located in the suburbs, 1.8 mi (2.8 km) from White Bear Yacht Club, and within 9 mi (15 km) of Maplewood Mall and ...

            Best Western Plus White Bear Country Inn$99

            Best Western Plus White Bear Country Inn$99
            Americas Best Value Inn-Stillwater/St. Paul

            Americas Best Value Inn-Stillwater/St. Paul

            1750 Frontage Rd W, Stillwater
              2.0 out of 5.0
               
               

              Situated in Stillwater, this hotel is within 12 mi (20 km) of StoneRidge Golf Club, Seasons on St. Croix Gallery, and Phipps Center for the Arts. Maplewood Mall ...

              Americas Best Value Inn-Stillwater/St. Paul$59

              Americas Best Value Inn-Stillwater/St. Paul$59
              AmericInn by Wyndham Forest Lake

              AmericInn by Wyndham Forest Lake

              1291 W Broadway Ave, Forest Lake
                2.5 out of 5.0
                 
                 

                Located in the heart of Forest Lake, this hotel is within 25 mi (40 km) of William O'Brien State Park, National Sports Center, and Maplewood Mall. Keller Golf ...

                AmericInn by Wyndham Forest Lake$85

                AmericInn by Wyndham Forest Lake$85
                Hampton Inn & Suites Lino Lakes

                Hampton Inn & Suites Lino Lakes

                579 Apollo Dr, Lino Lakes
                  2.5 out of 5.0
                   
                   

                  Situated in Lino Lakes, this hotel is within 20 mi (32 km) of University of Minnesota-St. Paul, University of Minnesota-Minneapolis, and Mill Ruins Park. Hamline ...

                  Hampton Inn & Suites Lino Lakes$101

                  Hampton Inn & Suites Lino Lakes$101
                  AmericInn by Wyndham White Bear Lake St. Paul

                  AmericInn by Wyndham White Bear Lake St. Paul

                  4675 White Bear Pkwy, White Bear Lake
                    2.0 out of 5.0
                     
                     

                    Situated near the beach, this hotel is within 9 mi (15 km) of White Bear Yacht Club, Maplewood Mall, and Keller Golf Course. Xcel Energy Center and Phalen Beach ...

                    AmericInn by Wyndham White Bear Lake St. Paul$99

                    AmericInn by Wyndham White Bear Lake St. Paul$99
                    AmericInn by Wyndham North Branch

                    AmericInn by Wyndham North Branch

                    38675 14th Ave, North Branch
                      2.5 out of 5.0
                       
                       

                      Situated in North Branch, this hotel is within 20 mi (32 km) of Wild Mountain Winery, WineHaven Winery and Vineyard, and Wild Mountain. Purple Hawk Country Club ...

                      AmericInn by Wyndham North Branch$110

                      AmericInn by Wyndham North Branch$110

                      Top Flight Deals

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