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Lakeside Vacations

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

Hotwire can help you find your travel bliss with Lakeside 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 Lakeside

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 Lakeside 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 Lakeside well.

Lakeside Flight + Hotel packages

Top Hotel Deals

See all 144 Hotels in Lakeside
Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

777 Blue Chip Drive, Michigan City
    3.5 out of 5.0
     
     

    Situated in Michigan City, this spa hotel is within 1 mi (2 km) of Washington Park Zoo and Lighthouse Place Premium Outlets. Whittaker Woods Golf Course and ...

    Blue Chip Casino Hotel and Spa$80

    Blue Chip Casino Hotel and Spa$80
    Baymont by Wyndham Michigan City

    Baymont by Wyndham Michigan City

    4128 South Franklin Street, Michigan City
      2.0 out of 5.0
       
       

      Located in the heart of Michigan City, this hotel is 2.6 mi (4.2 km) from Lighthouse Place Premium Outlets and within 9 mi (15 km) of Washington Park Zoo and ...

      Baymont by Wyndham Michigan City$58

      Baymont by Wyndham Michigan City$58
      Baymont by Wyndham New Buffalo

      Baymont by Wyndham New Buffalo

      18800 Harbor Country Drive, New Buffalo
        2.5 out of 5.0
         
         

        Situated in New Buffalo, this hotel is 1.3 mi (2.1 km) from New Buffalo Public Beach and 2.2 mi (3.5 km) from Whittaker Woods Golf Course. Legacy Hills Golf ...

        Baymont by Wyndham New Buffalo$62

        Baymont by Wyndham New Buffalo$62
        Microtel Inn & Suites by Wyndham Michigan City

        Microtel Inn & Suites by Wyndham Michigan City

        9834 W 400 N, Michigan City
          2.0 out of 5.0
           
           

          Situated in Michigan City, this hotel is within 9 mi (15 km) of Lighthouse Place Premium Outlets, Washington Park Zoo, and Legacy Hills Golf Club. Indiana Dunes ...

          Microtel Inn & Suites by Wyndham Michigan City$71

          Microtel Inn & Suites by Wyndham Michigan City$71
          Super 8 by Wyndham South Bend

          Super 8 by Wyndham South Bend

          4124 Ameritech Drive, South Bend
            2.0 out of 5.0
             
             

            Situated in South Bend, this motel is within 6 mi (10 km) of Clay Township Park, South Bend Military Honor Park and Museum, and Roseland Town Park. Kennedy Park ...

            Super 8 by Wyndham South Bend$41

            Super 8 by Wyndham South Bend$41
            Fairfield Inn & Suites by Marriott New Buffalo

            Fairfield Inn & Suites by Marriott New Buffalo

            11400 Holiday Drive, New Buffalo
              2.5 out of 5.0
               
               

              Situated in New Buffalo, this hotel is 1.5 mi (2.5 km) from New Buffalo Public Beach and 2.2 mi (3.6 km) from Whittaker Woods Golf Course. Legacy Hills Golf ...

              Fairfield Inn & Suites by Marriott New Buffalo$89

              Fairfield Inn & Suites by Marriott New Buffalo$89
              Country Inn & Suites by Radisson, Michigan City, IN

              Country Inn & Suites by Radisson, Michigan City, IN

              3805 North Frontage Road, Michigan City
                3.0 out of 5.0
                 
                 

                Situated in Michigan City, this hotel is within 9 mi (15 km) of Lighthouse Place Premium Outlets, Washington Park Zoo, and Legacy Hills Golf Club. Indiana Dunes ...

                Country Inn & Suites by Radisson, Michigan City, IN$71

                Country Inn & Suites by Radisson, Michigan City, IN$71
                Comfort Inn

                Comfort Inn

                18830 Laporte Rd, New Buffalo
                  2.5 out of 5.0
                   
                   

                  Located in the heart of New Buffalo, this hotel is 1.4 mi (2.2 km) from New Buffalo Public Beach and 2.1 mi (3.4 km) from Whittaker Woods Golf Course. Legacy ...

                  Comfort Inn$85

                  Comfort Inn$85
                  Holiday Inn Express & Suites St Joseph

                  Holiday Inn Express & Suites St Joseph

                  3019 Lakeshore Drive, Saint Joseph
                    2.5 out of 5.0
                     
                     

                    Situated in Saint Joseph, this hotel is within 6 mi (10 km) of Lakeland Regional Medical Center, Silver Beach, and Harbor Shores Golf Club. Lake Michigan College ...

                    Holiday Inn Express & Suites St Joseph$115

                    Holiday Inn Express & Suites St Joseph$115
                    SpringHill Suites Benton Harbor St. Joseph

                    SpringHill Suites Benton Harbor St. Joseph

                    1255 Cinema Way, Benton Harbor
                      3.0 out of 5.0
                       
                       

                      Situated in Benton Harbor, this hotel is within 6 mi (10 km) of Lake Michigan College, Lakeland Regional Medical Center, and Harbor Shores Golf Club. Silver ...

                      SpringHill Suites Benton Harbor St. Joseph$94

                      SpringHill Suites Benton Harbor St. Joseph$94

                      Top Flight Deals

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