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Oskaloosa Vacations

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

Hotwire can help you find your travel bliss with Oskaloosa 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 Oskaloosa

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 Oskaloosa 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 Oskaloosa well.

Top Hotel Deals

See all 17 Hotels in Oskaloosa
EverSpring Inn & Suites

EverSpring Inn & Suites

2401 A Ave West, Oskaloosa
    2.5 out of 5.0
     
     

    Located in the heart of Oskaloosa, this hotel is 1.2 mi (1.9 km) from VanderWilt Park and within 3 mi (5 km) of City Square Park and Edmundson Golf Course. Tassel ...

    EverSpring Inn & Suites$110

    EverSpring Inn & Suites$110
    Oskaloosa Motel

    Oskaloosa Motel

    2278 Highway 63 North, Oskaloosa
      2.5 out of 5.0
       
       

      Situated in Oskaloosa, this motel is 2.2 mi (3.5 km) from City Square Park and 2.4 mi (3.8 km) from VanderWilt Park. Edmundson Golf Course and Tassel Ridge Winery ...

      Americas Best Value Inn-Oskaloosa

      Americas Best Value Inn-Oskaloosa

      1315 A Avenue East, Oskaloosa
        2.0 out of 5.0
         
         

        Situated in Oskaloosa, this hotel is 0.9 mi (1.4 km) from City Square Park and within 3 mi (5 km) of VanderWilt Park and Edmundson Golf Course. Tassel Ridge ...

        Super 8 by Wyndham Oskaloosa IA

        Super 8 by Wyndham Oskaloosa IA

        306 S 17th St, Oskaloosa
          2.0 out of 5.0
           
           

          Situated in Oskaloosa, this hotel is within 3 mi (5 km) of City Square Park, Edmundson Golf Course, and VanderWilt Park. Tassel Ridge Winery is 7.7 mi (12.4 ...

          Super 8 by Wyndham Oskaloosa IA$80

          Super 8 by Wyndham Oskaloosa IA$80
          Budget Inn Oskaloosa

          Budget Inn Oskaloosa

          1210 A Avenue East, Oskaloosa
            2.0 out of 5.0
             
             

            Situated in Oskaloosa, this motel is 0.8 mi (1.3 km) from City Square Park and within 3 mi (5 km) of VanderWilt Park and Edmundson Golf Course. Tassel Ridge ...

            Lexington Inn and Suites - Ottumwa

            Lexington Inn and Suites - Ottumwa

            2813 N Court Street, Ottumwa
              3.0 out of 5.0
               
               

              Situated in Ottumwa, this hotel is 2.5 mi (4.1 km) from Memorial Park and 3.1 mi (4.9 km) from Wapello County Historical Museum. Davis County Historical Society ...

              Lexington Inn and Suites - Ottumwa$62

              Lexington Inn and Suites - Ottumwa$62
              Baymont by Wyndham Pella

              Baymont by Wyndham Pella

              2104 Washington St, Pella
                2.5 out of 5.0
                 
                 

                Situated in the historical district, this hotel is within 20 mi (32 km) of Peace Tree Brewing Company, Tassel Ridge Winery, and National Sprint Car Hall of Fame. ...

                Baymont by Wyndham Pella$75

                Baymont by Wyndham Pella$75
                Dutch Mill Inn

                Dutch Mill Inn

                205 Oskaloosa, Pella
                  2.5 out of 5.0
                   
                   

                  Situated in Pella, this motel is within 16 mi (25 km) of Tassel Ridge Winery, Peace Tree Brewing Company, and VanderWilt Park. City Square Park and Edmundson ...

                  AmericInn by Wyndham Pella

                  AmericInn by Wyndham Pella

                  910 W 16th US 163 Exit 40, Pella
                    2.5 out of 5.0
                     
                     

                    Situated in Pella, this hotel is 12.5 mi (20.2 km) from Peace Tree Brewing Company and 16.4 mi (26.4 km) from National Sprint Car Hall of Fame.

                    AmericInn by Wyndham Pella$90

                    AmericInn by Wyndham Pella$90
                    Country Inn & Suites by Radisson, Pella, IA

                    Country Inn & Suites by Radisson, Pella, IA

                    315 Roosevelt Road, Pella
                      2.5 out of 5.0
                       
                       

                      Situated in Pella, this hotel is within 16 mi (25 km) of Tassel Ridge Winery, Peace Tree Brewing Company, and VanderWilt Park. City Square Park and Edmundson ...

                      Country Inn & Suites by Radisson, Pella, IA$109

                      Country Inn & Suites by Radisson, Pella, IA$109

                      Top Flight Deals

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