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Cumberland Beach Vacations

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

Hotwire can help you find your travel bliss with Cumberland Beach 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 Cumberland Beach

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 Cumberland Beach 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 Cumberland Beach well.

Top Hotel Deals

See all 54 Hotels in Cumberland Beach
Cardinal Motel

Cardinal Motel

8906 11 Highway South, Cumberland Beach
    2.5 out of 5.0
     
     

    Situated near the beach, this motel is within 6 mi (10 km) of Orillia Square Mall, Hawk Ridge Golf and Country Club, and Couchiching Golf and Country Club. Orillia ...

    Days Inn by Wyndham Orillia

    Days Inn by Wyndham Orillia

    5850 Rama Road, Ramara
      2.5 out of 5.0
       
       

      Situated in Ramara, this hotel is 0.4 mi (0.6 km) from Casino Rama and within 6 mi (10 km) of Mara Provincial Park and Leacock Museum. Orillia Opera House and ...

      Days Inn by Wyndham Orillia$100

      Days Inn by Wyndham Orillia$100
      Stone Gate Inn

      Stone Gate Inn

      437 Laclie Street, Orillia
        3.5 out of 5.0
         
         

        Located in the heart of Orillia, this hotel is 0.7 mi (1.1 km) from Couchiching Golf and Country Club and 1.5 mi (2.5 km) from Orillia Opera House. Orillia Square ...

        Stone Gate Inn$101

        Stone Gate Inn$101
        Horseshoe Resort

        Horseshoe Resort

        1101 Horseshoe Valley Road, Barrie
          3.0 out of 5.0
           
           

          This Barrie resort is on the beach, 0.2 mi (0.2 km) from Horseshoe Valley, and within 12 mi (20 km) of Heritage Hills Golf Club and Hardwood Ski and Bike. Mount ...

          Horseshoe Resort$84

          Horseshoe Resort$84
          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
            Highwayman Inn & Conference Centre

            Highwayman Inn & Conference Centre

            201 Woodside Drive, Orillia
              3.0 out of 5.0
               
               

              Situated in Orillia, this hotel is within 1 mi (2 km) of Orillia Community Centre Arena and Orillia Opera House. Couchiching Golf and Country Club and Orillia ...

              Highwayman Inn & Conference Centre$75

              Highwayman Inn & Conference Centre$75
              Best Western Plus Orillia Hotel

              Best Western Plus Orillia Hotel

              440 Couchiching Point Rd, Orillia
                3.0 out of 5.0
                 
                 

                Situated in Orillia, this eco-friendly hotel is 1 mi (1.6 km) from Leacock Museum and 2.3 mi (3.8 km) from Orillia Opera House. Mara Provincial Park and Orillia ...

                Best Western Plus Orillia Hotel$109

                Best Western Plus Orillia Hotel$109
                Econo Lodge Orillia

                Econo Lodge Orillia

                265 Memorial Ave, Orillia
                  1.5 out of 5.0
                   
                   

                  Located in the heart of Orillia, this hotel is within 3 mi (5 km) of Orillia Opera House, Leacock Museum, and Couchiching Golf and Country Club. Orillia Square ...

                  Econo Lodge Orillia$54

                  Econo Lodge Orillia$54
                  Carriage Ridge Resort & Carriage Hills at Horseshoe Valley

                  Carriage Ridge Resort & Carriage Hills at Horseshoe Valley

                  90 Highland Drive, Oro-Medonte
                    3.0 out of 5.0
                     
                     

                    Conveniently located near the ski slopes, this Oro-Medonte condo resort is 2.1 mi (3.4 km) from Horseshoe Valley and within 12 mi (20 km) of Simcoe County Museum ...

                    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$84

                      Howard Johnson by Wyndham Gravenhurst$84

                      Top Flight Deals

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