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Windermere Vacations

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

Hotwire can help you find your travel bliss with Windermere 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 Windermere

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 Windermere 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 Windermere well.

Top Hotel Deals

See all 77 Hotels in Windermere
Windermere House

Windermere House

2508 Windermere Road, Windermere
    3.5 out of 5.0
     
     

    Located in Muskoka Lakes, this beachfront resort is next to a golf course, just steps from Windermere Marina and Windermere Golf & Country Club. Dee Bank Falls ...

    Windermere House$181

    Windermere House$181
    The Baldwins Resort

    The Baldwins Resort

    1024 Golf Avenue Rd., Windermere
      2.5 out of 5.0
       
       

      This Muskoka Lakes cottage is located next to a golf course, nestled on the beach a short distance from Windermere Golf & Country Club, Windermere Marina, and ...

      Muskoka Shores Cottages

      Muskoka Shores Cottages

      1046 Cowan Park Drive, Windermere
        3.5 out of 5.0
         
         

        This Muskoka Lakes cottage is on the beach, 2.6 mi (4.2 km) from Dee Bank Falls, and within 6 mi (10 km) of Windermere Marina and Windermere Golf & Country Club. ...

        JW Marriott The Rosseau Muskoka Resort & Spa

        JW Marriott The Rosseau Muskoka Resort & Spa

        1050 Paignton House Road, Minett
          4.5 out of 5.0
           
           

          Nestled on the beach, this Minett resort is within 1 mi (2 km) of The Rock Golf Course and Muskoka Sports and Recreation. The Port Carling Wall and Muskoka Lakes ...

          JW Marriott The Rosseau Muskoka Resort & Spa$173

          JW Marriott The Rosseau Muskoka Resort & Spa$173
          Holiday Inn Express & Suites Huntsville

          Holiday Inn Express & Suites Huntsville

          100 Howland Dr, Huntsville
            2.5 out of 5.0
             
             

            Situated in Huntsville, this hotel is within 3 mi (5 km) of Huntsville Civic Center Algonquin Theater, Muskoka Heritage Place, and Huntsville Downs Golf & Country ...

            Holiday Inn Express & Suites Huntsville$85

            Holiday Inn Express & Suites Huntsville$85
            Residence Inn by Marriott Gravenhurst Muskoka Wharf

            Residence Inn by Marriott Gravenhurst Muskoka Wharf

            285 Steamship Bay Road, Gravenhurst
              3.0 out of 5.0
               
               

              Situated in Gravenhurst, this hotel is steps from Muskoka Boat and Heritage Centre and Muskoka Wharf. Muskoka Steamships and Bethure Memorial House are also ...

              Residence Inn by Marriott Gravenhurst Muskoka Wharf$108

              Residence Inn by Marriott Gravenhurst Muskoka Wharf$108
              Best Western Plus Muskoka Inn

              Best Western Plus Muskoka Inn

              86 Howland Dr, Huntsville
                2.5 out of 5.0
                 
                 

                Situated near the beach, this hotel is within 3 mi (5 km) of Huntsville Civic Center Algonquin Theater, Muskoka Heritage Place, and Huntsville Downs Golf & Country ...

                Best Western Plus Muskoka Inn$100

                Best Western Plus Muskoka Inn$100
                Howard Johnson by Wyndham Gravenhurst

                Howard Johnson by Wyndham Gravenhurst

                1165 Muskoka Rd South, Gravenhurst
                  2.0 out of 5.0
                   
                   

                  Situated in Gravenhurst, this motel is within 1 mi (2 km) of Gravenhurst Opera House, Gull Lake Rotary Park, and Bethure Memorial House. Muskoka Steamships and ...

                  Howard Johnson by Wyndham Gravenhurst$93

                  Howard Johnson by Wyndham Gravenhurst$93
                  Motel 6 Huntsville

                  Motel 6 Huntsville

                  70 Howland Drive, Huntsville
                    2.0 out of 5.0
                     
                     

                    Situated in Huntsville, this hotel is within 3 mi (5 km) of Huntsville Civic Center Algonquin Theater, Muskoka Heritage Place, and Huntsville Downs Golf & Country ...

                    Motel 6 Huntsville$69

                    Motel 6 Huntsville$69
                    Econo Lodge

                    Econo Lodge

                    117 Main St W, Huntsville
                      2.0 out of 5.0
                       
                       

                      Located in the heart of Huntsville, this hotel is within 1 mi (2 km) of Huntsville Civic Center Algonquin Theater and Muskoka Heritage Place. Huntsville Downs ...

                      Econo Lodge$47

                      Econo Lodge$47

                      Top Flight Deals

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