Cottages in Caledon and Estates - Holiday Lettings - Holiday Rentals Caledon

Close

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

88 Holiday homes

    17

    Apartment rental in Caledon

    Ontario / Caledon

    1 3 2 nights min

    • 1 bedroom
    • sleeps 3
    • 2 nights min
    • Child friendly
    • Air conditioning

    from £39 / night

    £270 / week

    Book View

    Responds fast!
    avg. 1 hour 53 minutes

    from £39 / night

    (2) Excellent 

      16

      Caledon holiday b&b rental

      Ontario / Caledon

      2 4 1 night min

      • 2 bedrooms
      • sleeps 4
      • 1 night min
      • Child friendly
      • Air conditioning
      • Private garden

      from £147 / night

      £1,029 / week

      Book View

      from £147 / night

        5

        Caravan/mobile home rental in Bolton

        Caledon / Bolton

        1 1 1 night min

        • 1 bedroom
        • sleeps 1
        • 1 night min
        • Child friendly
        • Air conditioning

        from £228 / night

        £1,300 / week

        Book View

        from £228 / night

          24

          Caledon holiday home let

          Ontario / Caledon

          2 5 1 night min

          • 2 bedrooms
          • sleeps 5
          • 1 night min
          • Child friendly
          • Air conditioning

          from £45 / night

          £316 / week

          Book View

          Responds fast!
          avg. 1 hour 53 minutes

          from £45 / night

          (1) Excellent 

            14

            Caledon holiday hotel apartment rental

            Ontario / Caledon

            1 4 1 night min

            • 1 bedroom
            • sleeps 4
            • 1 night min
            • Child friendly
            • Air conditioning

            from £98 / night

            £683 / week

            Book View

            from £98 / night

              15

              Hotel apartment rental in Caledon

              Ontario / Caledon

              1 3 1 night min

              • 1 bedroom
              • sleeps 3
              • 1 night min
              • Child friendly
              • Air conditioning

              from £98 / night

              £686 / week

              Book View

              from £98 / night

                17

                Caledon holiday log cabin rental

                Ontario / Caledon

                1 2 1 night min

                • 1 bedroom
                • sleeps 2
                • 1 night min

                from £73 / night

                £429 / week

                Book View

                from £73 / night

                Great rentals within 20 miles that match your search

                Distance approx 16.39 miles from Caledon

                  6

                  Woodbridge holiday apartment rental

                  Vaughan / Woodbridge

                  1 4 7 nights min

                  • 1 bedroom
                  • sleeps 4
                  • 7 nights min
                  • Child friendly
                  • Air conditioning

                  from £52 / night

                  £325 - £416 / week

                  Book View

                  from £52 / night

                  Distance approx 11.44 miles from Caledon Show on Map

                    16

                    Holiday home in Brampton

                    Ontario / Brampton

                    4 7 2 nights min

                    • 4 bedrooms
                    • sleeps 7
                    • 2 nights min
                    • Child friendly
                    • Air conditioning

                    from £147 / night

                    £1,024 / week

                    Book View

                    from £147 / night

                    Distance approx 15.9 miles from Caledon Show on Map

                      19

                      Holiday home in Georgetown

                      Halton Hills / Georgetown

                      2 4 2 nights min

                      • 2 bedrooms
                      • sleeps 4
                      • 2 nights min
                      • Child friendly
                      • Air conditioning

                      from £62 / night

                      £433 / week

                      Book View

                      from £62 / night

                      Distance approx 10.47 miles from Caledon Show on Map

                        21

                        Brampton holiday home rental

                        Ontario / Brampton

                        4 10 3 nights min

                        • 4 bedrooms
                        • sleeps 10
                        • 3 nights min
                        • Child friendly
                        • Air conditioning
                        • Private garden

                        from £88 / night

                        £553 - £1,769 / week

                        Book View

                        from £88 / night

                        Distance approx 9.09 miles from Caledon Show on Map

                          19

                          Holiday home in Brampton

                          Ontario / Brampton

                          4 8 2 nights min

                          • 4 bedrooms
                          • sleeps 8
                          • 2 nights min
                          • Child friendly
                          • Air conditioning

                          from £147 / night

                          £1,024 / week

                          Book View

                          from £147 / night

                          Distance approx 12.61 miles from Caledon Show on Map

                            15

                            Brampton holiday home accommodation

                            Ontario / Brampton

                            3 6 2 nights min

                            • 3 bedrooms
                            • sleeps 6
                            • 2 nights min
                            • Child friendly
                            • Air conditioning

                            from £121 / night

                            £842 / week

                            Book View

                            from £121 / night

                            Distance approx 19.7 miles from Caledon

                              18

                              Holiday home in Toronto

                              Ontario / Toronto

                              1 3 5 nights min

                              • 1 bedroom
                              • sleeps 3
                              • 5 nights min
                              • Child friendly
                              • Air conditioning
                              • Private garden

                              from £32 / night

                              £221 - £312 / week

                              Book View

                              from £32 / night

                              Distance approx 19.61 miles from Caledon

                                26

                                Orangeville holiday farmhouse rental

                                Ontario / Orangeville

                                5 12 1 night min

                                • 5 bedrooms
                                • sleeps 12
                                • 1 night min
                                • Child friendly
                                • Air conditioning
                                • Private garden

                                from £355 / night

                                £2,480 / week

                                Book View

                                from £355 / night

                                Distance approx 13.47 miles from Caledon Show on Map

                                  15

                                  Brampton holiday home rental

                                  Ontario / Brampton

                                  4 10 2 nights min

                                  • 4 bedrooms
                                  • sleeps 10
                                  • 2 nights min
                                  • Child friendly
                                  • Air conditioning
                                  • Private garden

                                  from £97 / night

                                  £650 - £878 / week

                                  Book View

                                  from £97 / night

                                  Distance approx 11.64 miles from Caledon Show on Map

                                    8

                                    Holiday home in Brampton

                                    Ontario / Brampton

                                    3 5 2 nights min

                                    • 3 bedrooms
                                    • sleeps 5
                                    • 2 nights min
                                    • Child friendly
                                    • Air conditioning

                                    from £121 / night

                                    £842 / week

                                    Book View

                                    from £121 / night

                                    Distance approx 14.77 miles from Caledon

                                      34

                                      Kleinburg holiday home rental

                                      Vaughan / Kleinburg

                                      4 18 3 nights min

                                      • 4 bedrooms
                                      • sleeps 18
                                      • 3 nights min
                                      • Child friendly
                                      • Air conditioning
                                      • Private garden

                                      from £130 / night

                                      £845 - £1,882 / week

                                      Book View

                                      Responds fast!
                                      avg. 3 hours 28 minutes

                                      from £130 / night

                                      Distance approx 10.25 miles from Caledon Show on Map

                                        15

                                        Home rental in Brampton

                                        Ontario / Brampton

                                        3 6 2 nights min

                                        • 3 bedrooms
                                        • sleeps 6
                                        • 2 nights min
                                        • Child friendly
                                        • Air conditioning

                                        from £120 / night

                                        £840 / week

                                        Book View

                                        from £120 / night

                                        Distance approx 14.7 miles from Caledon Show on Map

                                          15

                                          Holiday home rental

                                          Ontario / Brampton

                                          3 6 2 nights min

                                          • 3 bedrooms
                                          • sleeps 6
                                          • 2 nights min
                                          • Child friendly

                                          from £121 / night

                                          £842 / week

                                          Book View

                                          from £121 / night

                                          Distance approx 17.14 miles from Caledon

                                            5

                                            Holiday home in Brampton

                                            Ontario / Brampton

                                            1 2 1 night min

                                            • 1 bedroom
                                            • sleeps 2
                                            • 1 night min
                                            • Child friendly
                                            • Air conditioning

                                            from £65 / night

                                            £455 / week

                                            Book View

                                            from £65 / night

                                            Distance approx 12.6 miles from Caledon Show on Map

                                              15

                                              Holiday home in Brampton

                                              Ontario / Brampton

                                              1 3 1 night min

                                              • 1 bedroom
                                              • sleeps 3
                                              • 1 night min
                                              • Child friendly
                                              • Air conditioning

                                              from £30 / night

                                              £205 / week

                                              Book View

                                              Responds fast!
                                              avg. 2 hours 3 minutes

                                              from £30 / night

                                              Distance approx 12.61 miles from Caledon Show on Map

                                                12

                                                Holiday home in Brampton

                                                Ontario / Brampton

                                                1 3 1 night min

                                                • 1 bedroom
                                                • sleeps 3
                                                • 1 night min
                                                • Child friendly
                                                • Air conditioning

                                                from £25 / night

                                                £173 / week

                                                Book View

                                                Responds fast!
                                                avg. 2 hours 3 minutes

                                                from £25 / night

                                                Distance approx 12.62 miles from Caledon Show on Map

                                                  10

                                                  Home rental in Brampton

                                                  Ontario / Brampton

                                                  1 2 1 night min

                                                  • 1 bedroom
                                                  • sleeps 2
                                                  • 1 night min
                                                  • Child friendly
                                                  • Air conditioning

                                                  from £26 / night

                                                  £182 / week

                                                  Book View

                                                  Responds fast!
                                                  avg. 2 hours 3 minutes

                                                  from £26 / night

                                                  Distance approx 15.79 miles from Caledon

                                                  (3) Excellent 

                                                    40

                                                    Holiday studio in Schomberg

                                                    Ontario / Schomberg

                                                    Studio 2 1 night min

                                                    • Studio
                                                    • sleeps 2
                                                    • 1 night min
                                                    • Nearest beach 44 km
                                                    • Child friendly
                                                    • Pet friendly

                                                    from £75 / night

                                                    £439 / week

                                                    Book View

                                                    from £75 / night

                                                    Distance approx 15.35 miles from Caledon

                                                      17

                                                      Woodbridge holiday home rental

                                                      Vaughan / Woodbridge

                                                      3 8 min stay varies

                                                      • 3 bedrooms
                                                      • sleeps 8
                                                      • min stay varies
                                                      • Child friendly
                                                      • Air conditioning
                                                      • Private garden

                                                      from £121 / night

                                                      £780 - £813 / week

                                                      Book View

                                                      Responds fast!
                                                      avg. 16 minutes

                                                      from £121 / night

                                                      Distance approx 15.78 miles from Caledon

                                                      (5) Excellent 

                                                      Certificate of Excellence

                                                        26

                                                        Holiday guest house in Schomberg

                                                        Ontario / Schomberg

                                                        1 6 1 night min

                                                        • 1 bedroom
                                                        • sleeps 6
                                                        • 1 night min
                                                        • Nearest beach 44 km
                                                        • Child friendly
                                                        • Air conditioning

                                                        Certificate of Excellence

                                                        from £75 / night

                                                        £455 / week

                                                        Book View

                                                        from £75 / night

                                                        Distance approx 10.96 miles from Caledon Show on Map

                                                        (1) Excellent 

                                                          17

                                                          Holiday home in Brampton

                                                          Ontario / Brampton

                                                          4 12 3 nights min

                                                          • 4 bedrooms
                                                          • sleeps 12
                                                          • 3 nights min
                                                          • Child friendly
                                                          • Air conditioning
                                                          • Private garden

                                                          from £147 / night

                                                          £1,024 / week

                                                          Book View

                                                          Responds fast!
                                                          avg. 1 hour 41 minutes

                                                          from £147 / night

                                                          Distance approx 10.34 miles from Caledon

                                                          (1) Excellent 

                                                            6

                                                            Holiday cottage in Schomberg

                                                            Ontario / Schomberg

                                                            1 2 1 night min

                                                            • 1 bedroom
                                                            • sleeps 2
                                                            • 1 night min
                                                            • Beach / lakeside relaxation
                                                            • Nearest beach 0 km
                                                            • Child friendly

                                                            from £98 / night

                                                            £650 - £923 / week

                                                            Book View

                                                            Responds fast!
                                                            avg. 1 hour 39 minutes

                                                            from £98 / night

                                                            Distance approx 16.26 miles from Caledon

                                                            (3) Very Good 

                                                              26

                                                              Ski farmhouse to rent in Alliston

                                                              New Tecumseth / Alliston

                                                              4 7 2 nights min

                                                              • 4 bedrooms
                                                              • sleeps 7
                                                              • 2 nights min
                                                              • Ski
                                                              • Child friendly
                                                              • Air conditioning

                                                              from £242 / night

                                                              £1,693 / week

                                                              Book View

                                                              Responds fast!
                                                              avg. 1 hour 25 minutes

                                                              from £242 / night

                                                              Distance approx 9.7 miles from Caledon Show on Map

                                                                49

                                                                Holiday castle in Brampton

                                                                Ontario / Brampton

                                                                12 28 1 night min

                                                                • 12 bedrooms
                                                                • sleeps 28
                                                                • 1 night min
                                                                • Child friendly
                                                                • Air conditioning
                                                                • Private garden

                                                                from £1,300 / night

                                                                £8,450 - £10,703 / week

                                                                Book View

                                                                Responds fast!
                                                                avg. 2 hours 58 minutes

                                                                from £1,300 / night

                                                                Distance approx 10.58 miles from Caledon

                                                                  11

                                                                  Holiday home in Brampton

                                                                  Ontario / Brampton

                                                                  5 16 2 nights min

                                                                  • 5 bedrooms
                                                                  • sleeps 16
                                                                  • 2 nights min
                                                                  • Child friendly
                                                                  • Air conditioning
                                                                  • Private garden

                                                                  from £386 / night

                                                                  £2,699 / week

                                                                  Book View

                                                                  Responds fast!
                                                                  avg. 3 hours 24 minutes

                                                                  from £386 / night

                                                                  Distance approx 9.36 miles from Caledon Show on Map

                                                                  (1) Excellent 

                                                                    12

                                                                    Holiday home in Brampton

                                                                    Ontario / Brampton

                                                                    2 2 1 night min

                                                                    • 2 bedrooms
                                                                    • sleeps 2
                                                                    • 1 night min
                                                                    • Air conditioning

                                                                    from £39 / night

                                                                    £273 / week

                                                                    Book View

                                                                    Responds fast!
                                                                    avg. 22 minutes

                                                                    from £39 / night

                                                                    Distance approx 11.45 miles from Caledon

                                                                    (2) Excellent 

                                                                      32

                                                                      Holiday home rental

                                                                      Ontario / Brampton

                                                                      5 16 2 nights min

                                                                      • 5 bedrooms
                                                                      • sleeps 16
                                                                      • 2 nights min
                                                                      • Child friendly
                                                                      • Air conditioning
                                                                      • Private garden

                                                                      from £130 / night

                                                                      £910 / week

                                                                      Book View

                                                                      from £130 / night

                                                                      Distance approx 15.79 miles from Caledon

                                                                        9

                                                                        Schomberg holiday tented camp rental

                                                                        Ontario / Schomberg

                                                                        1 4 1 night min

                                                                        • 1 bedroom
                                                                        • sleeps 4
                                                                        • 1 night min
                                                                        • Nearest beach 44 km
                                                                        • Child friendly
                                                                        • Pet friendly

                                                                        from £26 / night

                                                                        £182 / week

                                                                        Book View

                                                                        from £26 / night

                                                                        Distance approx 17.07 miles from Caledon

                                                                          7

                                                                          Home rental in Toronto

                                                                          Ontario / Toronto

                                                                          1 1 90 nights min

                                                                          • 1 bedroom
                                                                          • sleeps 1
                                                                          • 90 nights min
                                                                          • Child friendly

                                                                          from £14 / night

                                                                          £98 / week

                                                                          Book View

                                                                          from £14 / night

                                                                          Distance approx 12.41 miles from Caledon

                                                                            9

                                                                            Ski studio to rent in Orangeville

                                                                            Ontario / Orangeville

                                                                            Studio 2 7 nights min

                                                                            • Studio
                                                                            • sleeps 2
                                                                            • 7 nights min
                                                                            • Ski
                                                                            • Child friendly

                                                                            from £51 / night

                                                                            £352 / week

                                                                            Book View

                                                                            from £51 / night

                                                                            Distance approx 14.52 miles from Caledon

                                                                              7

                                                                              Holiday home in Woodbridge

                                                                              Vaughan / Woodbridge

                                                                              1 4 2 nights min

                                                                              • 1 bedroom
                                                                              • sleeps 4
                                                                              • 2 nights min
                                                                              • Child friendly
                                                                              • Air conditioning
                                                                              • Private garden

                                                                              from £39 / night

                                                                              £269 / week

                                                                              Book View

                                                                              from £39 / night

                                                                              Distance approx 16.71 miles from Caledon

                                                                                12

                                                                                Home rental in Brampton

                                                                                Ontario / Brampton

                                                                                3 5 1 night min

                                                                                • 3 bedrooms
                                                                                • sleeps 5
                                                                                • 1 night min
                                                                                • Child friendly
                                                                                • Air conditioning
                                                                                • Private garden

                                                                                from £114 / night

                                                                                £780 / week

                                                                                Book View

                                                                                from £114 / night

                                                                                Distance approx 11.61 miles from Caledon Show on Map

                                                                                  11

                                                                                  Home rental in Brampton

                                                                                  Ontario / Brampton

                                                                                  1 2 2 nights min

                                                                                  • 1 bedroom
                                                                                  • sleeps 2
                                                                                  • 2 nights min
                                                                                  • Child friendly

                                                                                  from £20 / night

                                                                                  £136 / week

                                                                                  Book View

                                                                                  from £20 / night

                                                                                  Also consider